PART 6 - Predictable Revenue...Predictable Revenue is the “Outbound Success Company”. We help...

P A R T 6

Outbound Sales Learnings from 2018

A complete guide of Predictable Revenue’s 2018 Podcasts

C O L L I N S T E W A R T

Predictable Revenue is the “Outbound Success Company”.

We help companies grow faster with Outbound Sales.

Our Co-Founder Aaron Ross is the author of the

book Predictable Revenue and was one of the first 150

employees at Salesforce where he built the outbound

methodology that is prac-ticed around the world in

sales teams today. Our other Co-Founder, Collin Stewart,

is the host of our weekly podcast where he interviews

B2B sales leaders on the biggest opportunities and challenges in the industry.

I N T R O

Collin Stewart, Co-Founder of Predictable Revenue.

Host of our weekly podcast.

We’ve taken all of our podcasts from 2018 and put them into a handy 6 part eBook. Learn how to overcome the biggest challenges facing B2B sales teams today, ensure you’re leveraging opportu-nities, and learn from best practices from industry leaders.

C O N T E N TP A R T 6

Editor’s note: this is part 6 of a

6-part series.

Why understanding the motivations of your different markets is critical to sales success

04

The more things change, the more they stay the same: Aaron Ross and Drift’s David Cancel on the future of sales

09

Clarity, Scalability, and Predictability: The Three Keys to Effective Sales Operations With Mesosphere’s David Hong

14

How to nail your proposals with Mimiran’s Reuben Swartz

19

Why Rambl’s Mitch Coopet believes sales and product teams are actually two sides of the same coin

24

The Sky’s the Limit: How, and Why, Sumo Finally Embraced Outbound Sales

28

How Zendesk’s Jaimie Buss is able to forecast revenue within 1% (at a $500 million company)

31

B2B Outbound Sales Learnings from 2018 - A complete guide of Predictable Revenue's 2018 Podcasts

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Why understanding the motivations of your different markets is critical to sales success

It’s such an obvious idea it can almost seem an afterthought: a sales team should always mold its strategy to suit

each of the markets it sells to.

After all, salespeople are always trying to connect with their prospects, and what better way than to speak their language and understand their concerns?Small businesses, mid-market firms, the always desirable enterprise – each comes with its own motivations (and quirks), and should be communicated with according to those traits.

Gabriel Moncayo. CEO and Co-Founder of sales education firm Always Hired.

At least that’s how it should be.The trouble with fast-moving sales teams is tactics, specifics, and gameplans can, some-times, fall by the wayside. There’s always time to strategize and draw up playbooks after the close, right?In a sense, of course, that’s true. Closing is what we’re here to do. But, without that institutional knowledge available to new and veteran salespeople alike, what are the dangers your company faces? What deals aren’t you closing as a result?“I started my career doing commercial sales in the nonprofit world. From there, I transitioned

https://predictablerevenue.com/podcast/053-tailoring-your-tactics-why-understanding-the-motivations-of-your-different-markets-is-critical-to-sales-success

B2B Outbound Sales Learnings from 2018 - A complete guide of Predictable Revenue's 2018 PodcastsB2B Outbound Sales Learnings from 2018 - A complete guide of Predictable Revenue's 2018 Podcasts

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to corporate sales and small business, and eventually to larger enterprise opportunities. To be very transparent, it was always very hard for me to ramp up. And it’s because I wasn’t applying unique tactics to the markets,” says Gabriel Moncayo, CEO and Co-Found-er of sales education firm Always Hired, on a recent edition of The Predictable Revenue Podcast.“After enough time of failing early on, I realized there was a lot of transferable skills between roles, but each opportunity was unique. And I was really trying to maximize myself at each role. You might put up a lot of activity metrics if you aren’t changing your approach, but when those metrics don’t translate to num-bers, there’s going to be some frustration.”

The different marketsThe road to tailoring your tactics to dif-ferent markets begins with defining what those different markets are.Full disclosure: there is loads of nuance in each market. Not all small businesses are the same, nor is every mid-market firm. But, for the purposes of this summary, we’re going to isolate potential markets to:Small business (on a subscription basis, these are deal sizes up to $500 per month);Mid-market (deal sizes ranging from $501 to $2K per month, again, on a subscription basis);Enterprise (more than 2K per month, on subscription)

Small business“This is a different type of buyer,” says Moncayo.“Selling to small business typically means you’re high on call volume – maybe 100 calls and 20 emails per day. And a lot of that activity is prob-ably based on follow ups, sending terms and things like that.”The reason for this high-octane selling, adds Moncayo, is because it’s easy to reach a decision maker.


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For example, if you sell to boutiques, the odds of you getting an owner on the phone during business hours is pretty good. The owners may be the primary staff members, working the floor as well as handling all of the back office responsibilities.As a result of that tightrope walk, small busi-ness owners are rarely at their desks, free to answer your prospecting emails.“They run around all day. They just aren’t around the computer,” says Moncayo.“Most of the emailing with them is to confirm an appointment, or send a proposal. But, typically, it’s not done to generate an appoint-ment.”While it may be easy to catch them with a quick phone call, the hectic life of a mom and pop shop owner does bring its own set of sig-nificant challenges – it can be difficult to get them to commit (and show up) to meetings.Something always comes up.

“I’ve worked for a company that sold to small business owners. We realized that a lot of customers had to reschedule, or would no-show. When we called them, they would say ‘sorry, I had to take my kid to class,’ or something like that,” says Moncayo.

“They weren’t used rescheduling appointments.”Once you do get a small business owner into a meeting,Moncayo says, it’s import-ant to understand that their buying de-cisions are often emotionally driven. The success of the business – every sale, every campaign, every breakthrough – directly impacts the owners and their family.

“From a high level, a small business owner’s priority is probably putting food on the table for the family. They are thinking about their family, and how their family will benefit from their immediate actions,” says Moncayo.“It is much more emotional. You will be communicating in ways that will relate back to their family. You won’t necessarily be com-municating in value props.”

The mid-marketMoving upstream to mid-size firms, however, means a change in tone and outreach. Unlike the personal aspect to small business sales, mid-market buyers are more focused on operation-al efficiencies, and how buying your good or service will help them con-tinue to grow. And that information is generally shared via email prospecting,


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as opposed to on-the-fly calls.Mid-market companies, adds Mon-cayo, are often trying to becoming enterprise organizations, so concise communication about how your com-pany can help them achieve that goal will resonate.“Now you’re likely dealing with compa-nies that generate millions and millions of dollars in revenue per year,” says Moncayo.“This requires a more logical approach to the sale. And it’s your job to apply that logic and illustrate how your tool will pro-duce the numbers they need them get them to where they need to go.”

But that data-driven approach, warns Moncayo, shouldn’t mean you aban-don all emotion in you’re selling. In a mid-market firm, you will likely be selling to members of the executive team – in some cases you may even be speaking with a founder. Those team members all have deep ties to the company, and are wholly focused on ensuring their ambitious targets are met.“These companies are grinding to become that hundred million dollar company. They want that status,” says Moncayo. “As a result, there is small emotional component of them trying to get to the next level.”

The enterprise The golden goose. The whale. The unicorn.

The prize catch every salesperson is looking to nab (thank you commission cheque!).But this sales cycle isn’t for the faint of

heart. It can be complex, requiring multiple meetings with different decision makers.

And unlike small businesses and mid-mar-ket companies, you’re like not dealing with founders or C-level executives. More often

than not, you’re selling to leaders of one department or business unit.

As such, this sale becomes even more operationally focused. You aren’t directly affecting the family of the owner, nor are

you giving the company a tool that will help catapult them to their next, long-desired

phase of growth.What you’re doing is helping one specific

team hit its goals.

“For an enterprise buyer, it’s a lot more val-ue driven. It’s all about the numbers. These buyers understand the concept of evaluat-ing multiple vendors, and they understand the concept of maximizing ROI. That is all

they are focused on,” says Moncayo.

“They are focused on creating efficiency with what they already have. So, you approach has

to be very data driven.”


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If there is any emotional pull at all in the enterprise sale, it’s that there are plenty of opportunities for face-to-face meet-ings. Because the deal size is significant, it’s worth it to hop on a plane and visit a prospect’s office, or make an appearance at a conference they are attending.You can afford to get to know your pros-pect, in person. You can present to their team. You can shake their hand.

“This is a big part of the process for an enterprise sales,” says Moncayo.“It make sense to spend a thousand dollars on a plane ticket to go see a prospect. It’s worth it.”

For more on Moncayo’s playbook for selling to different markets, check out his recent edition of The Predictable Revenue Podcast.




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The more things change, the more they stay the same: Aaron Ross and Drift’s David Cancel on the future of sales

It’s hard to imagine given the complex sales environment we’re currently nav-igating, but once upon a time, sales

methods were exceedingly simple: you either called a prospect on the phone, or you went to visit them.That was it.

Sure, closing those deals still required finesse and stalwart sales skills in nego-tiation, but there were no tools to help with qualification, list building, or demo presentations. It was just unmediated, hu-man-to-human selling.“I did door-to-door sales in high school and college. I had a painting gig, and did ad sales for the Stanford University newspaper. When I think about sales, that’s really where I started,” says Aaron Ross, in conversation

with Drift CEO David Cancel, on a recent webinar presented by Predictable Revenue and Drift.“Today, there is some things that have changed a lot – tools, techniques, and social channels, for instance. But, people are people. That doesn’t change. How people interact with other people stays constant.”Like Aaron, David’s professional journey began long before the Internet became an omnipresent force. Although trained as an en-gineer, David says he enjoyed talking to sales and marketing professionals – understanding what they do, and how often difficult day-to-day could be improved.“I’ve never been in sales. I discovered I had this talent as an engineer, but I really liked talking to sales and marketing people,” says David.

https://predictablerevenue.com/podcast/069-the-more-things-change-the-more-they-stay-the-same-aaron-ross-and-drifts-david-cancel-on-the-future-of-sales


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David Cancel.Drift CEO

“And so all the sales people I would work with, they would always told me I should work on their team. I never did, but I’m on my fifth company now, and each of them have been in the sales and marketing space to some degree.”

Marketing Qualified Lead vs. Product Qualified Lead vs. Conversation Qualified Lead

During David’s tenure at Hubspot (his company Performable was acquired by the inbound marketing and sales jugger-naut in 2011), he says he and his team were obsessed with understanding, and perfecting, the Marketing Qualified Lead and the inside sales model.The MQL, and its related processes, represent a landmark philosophy still widely used in the world of sales today. Instead of picking up the phone and cold calling unsuspecting prospects, why not entice potential customers with tailored marketing activities, have them share their contact information (captured in a form of some sort), and then call them?A warm lead is better than a cold one, right?

But, just as Hubspot was focused on the MQL, other companies such as Evernote and Dropbox were also re-fining interesting sales con-cepts such as the Product Qualified Lead, says David. And he, and his team, was inspired by their work.“We had this MQL model working pretty well. But, then we started thinking about the Product Qualified Lead. We were looking at Dropbox and Evernote and thought they were trying to build something like a PQL,” says David.

“They would get people in the door using the product for free, or from free trials. Then they would nurture them enough, send out enough sig-nals, that they would convert to paying customers.”

Over time, adds David, he began to design another type of lead: the Conver-sation Qualified Lead. The CQL, as it were, is just like a Marketing Qualified Lead,


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but instead of designing intricate nurturing processes for inbound leads, the CQL gets qualified by a quick conversation once the lead is captured by a form.“Why try and spend all of our time thinking about what prospects want, when we could just ask them?” says David.“Of course, we tested and researched a lot, but that was our thinking.”

The Importance of the SDR

Working all of these warm leads, and cold outbound ones too, is the Sales Develop-ment Representative. Like the creation of the MQL, the growth of the SDR is a critical development in the evolution of sales.Gone are the days of cold calling a pros-pect, and then getting in your car to visit their office to close the deal. Now, a veri-table army of trained prospectors qualify leads, learn their prospect’s needs, get them excited, and then hand them off to an Account Executive to close the deal.The system has proven so popular that nearly every modern tech company uses it (one glance at job postings reveals no shortage of SDR openings). At the risk of sounding arro-gant, part of that popularity is due to our very own Aaron Ross. But, warns Aaron, there are potential dangers in the SDR-AE framework.

“It can be done well, and it can be done poorly. One of the dangers is when AEs think they don’t need to prospect any-more. That’s not true,” says Aaron.

“You have to watch out for people over relying on their colleagues.”

Another challenging aspect of the SDR position, adds David, is measur-ing their success accurately. In fact, David says he’s never been able to do it properly and, as a result, never been convinced of the importance of the SDR in the first place.

“I’ve never been a huge fan of the SDR. At Hubspot, we had a lot of them. Now, we don’t have any. It needs to be measured correctly. People overreact to things – everyone says they need SDRs. And AEs think so too,” says David.“In the past, we were never able to really prove the profitability of the SDR. For me, I heard all of lines: you need them to prospect for enterprise deals, or it’s a great breeding ground for developing AEs. But, I was never really able to define the business benefit of them.”


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(Editor’s note: we chatted with Jaimie Buss, VP of North American Sales at Zendesk, on a previous podcast about the importance of the SDR. According to Buss, her company saw a 25% lift in revenue after instituting an SDR team. You can listen to our chat with Jaimie here, or read about it here).

Drift’s Use of Bots

You read that right – David’s com-pany Drift, which develops a cutting edge sales and marketing platform, doesn’t have any SDRs. None. How is that possible?Bots… that’s how.

“When we started out, we figured chat messaging could be used for sales.

It never really worked in the past for issues such as qualification, but we

wanted to see what we could do. So, we created this bot,” says David.

“I hated the idea at first, and I didn’t like what I saw of the bots in the market. In my experience, bots were always trying to convince you they

were human. They were given a name, for instance. But, it didn’t take long for you to realize they aren’t human. So, what we did was make sure it would always acknowl-edge itself as a bot. And, we thought that would change people’s expectations.”

A fundamental component to the suc-cess of a Drift bot, adds David, is the consistency of experience it provides. For example, when someone comes to the Drift website, the bots can ask the same qualifying question an SDR can. And, at some point, when it decides the person is qualified, it routes them to an AE.The company has also connected its bots to a booking system so a lead can easily book a meeting with an Account Executive. If a Drift’s AE isn’t available for a proposed meeting, the bot facil-itates a booking for the prospect at a better time.

“The first magical thing that hap-pened at Drift was when our first rep came in to the office, and their whole week was full of qualified demo ops that the bot qualified for them,” says David.

“And that can happen 24/7, 365.”


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A Human Touch

If this sounds like Drift has replaced SDRs with bots, it’s because they have. David says his com-pany has been able to place salespeople “in positions further down the funnel” because they haven’t needed to hire prospectors.But although some of the fundamental tasks of the SDR has been replaced by Drift’s bots, don’t count human out just yet. We still need ingenious humans to close deals, and come up with the breakthroughs that will change the space again.

“I think we see the advantage of AI. But, we also need things to stand out. If AI is doing everything, it will all seem the same,” says Aaron.“But the intuitive breakthroughs will always come from humans. It’s humans that come up with the ideas and projects that have never been done before.”David agrees.“The more we automate, the more we need human creativity. We need to stand out. As people go to dif-ferent channels or trends, we need humans to make the leap to something new,” says David.

“And, of course, it’s still people buying from people.”

For more on David and Aaron’s detailed, wide-rang-ing chat, check out their discussion on a recent edi-tion of The Predictable Revenue Podcast channel.




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Clarity, Scalability, and Predictability: The Three Keys to Effective Sales Operations With Mesosphere’s David Hong

David HongVice President of Field Opera-tions at Mesosphere

When you live and breathe sales development (as we do), it’s easy to get caught up in learning

and applying different nitty gritty tactics to make your sales cycle more efficient and effective. Every tweak, new approach, or innovative method can mean a better-run sales team.

And a better run sales team means more revenue.But while sales leaders and high-performing reps constantly work to evolve their process-es in the hopes of closing more deals, it’s the sales operations team that builds and main-tains the infrastructure necessary to keep the team organized and empowered to do their jobs.It’s a critical piece of the sales puzzle, even though it rarely, if ever, enjoys time in the spotlight.“I can’t remember when I first started in sales ops, but it’s definitely not a career you study in college or plan on getting into after school. People, typically, fall into the role, and that’s how I got into it,” says David Hong, Vice Pres-ident of Field Operations at Mesosphere, on a recent edition of The Predictable Revenue Podcast.

https://predictablerevenue.com/podcast/066-clarity-scalability-and-predictability-the-three-keys-to-effective-sales-operations-with-mesospheres-david-hong


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“We are the enablement function for the sales team, but also of the larger function of business operations. The way I look at sales ops is that we’re Switzerland in the company. That means, if our roles are structured prop-erly, is that we are not necessarily reporting into sales, finance, or operations. We are responsible for the data and the analytics, which gives sales ops a holistic and unbiased view of the metrics. That has always been my vision, and how I build my team.”

David’s principlesGoverning Hong’s day-to-day sales opera-tions work are three main principles:

CLARITY – this is, primarily, concerned with the various definitions the sales opera-tions teams uses in tools such as Salesforce. For example, are the sales cycle stages clearly defined and understood by everyone neces-sary?

SCALABILITY – as the team and product grows, what processes will break? For exam-ple, are the compensation plans being used with a team of 5 sales people ready for 10x more team members?

PREDICTABILITY – assessing and pro-viding feedback to the organization, in order

to determine where to best invest resources. For example, this includes considerations such as pipeline coverage, how much pipeline each individual rep can handle, and what the total addressable market in a particular region is.

A few of David’s projectsThose principles, of course, can be applied to a host different projects. For Hong, those projects include everything from sales processes and Salesforce stages, to exten-sive go-to-market strategies and designing a quote-to-cash system.

“Initially, it’s all about the sale process. Do you have the right

stages in place, and are the reps following the stages? That mor-phed into pipeline – do we have

the right amount of pipeline? How is each rep performing? Which territories are better than others?” says Hong.


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Another project, although still in the sandbox, adds Hong, is a simple Wizard in Salesforce that allows Mesosphere’s SDRs to check off different attributes associated with each SQL they handle. Based on the boxes they check, a score for each SQL can be generated, via a simple algorithm. That Salesforce data will give sales leaders the power to run reports on all SQLs, and the scores associated, so they can priori-tize particular deals in the pipeline.

“Yes, it is a nice tool for SDRs, but the real carrot here is to get them to input. Remem-

ber, when it comes to the workflow, you have to design them so sales reps can embed

them into their day,” says Hong.“If you can do that, than they will follow the processes. And, with this project specifically, what’s beneficial on the back end is we can run reports on all of SQLs, and their scores. This gave us that visibility into that data.”

MEDDPICC…and CHAMPArguably the most extensive sales oper-ations project Hong, and his team, imple-mented at Mesospehere is the MEDDPICC qualification method, used to qualify each opportunity in a rep’s pipeline. It serves as a guided opportunity checklist, measures the qualification process, as well as cus-tomer buy-in.Mesosphere’s MEDDPICC process is built in the opportunity object Salesforce, with a text field accompanying each of the letters highlighted below.

(Editor’s note: we had an in-depth discussion Zendesk’s Jaimie Buss about her design, and implementation of the MEDDPICC qualification system at Zendesk. Listen to the podcast here, or read about it here.)

“Then, we took a broader scope to our role, and started consid-ering the tools we use. Do we have the right tools? What are

the right tools? And, do you want to measure activities? Or, just opportunity creation? Lastly, we would work on go-to market strategies. For example, how do you know that marketing has a tight integration with sales? And, are the right leads flowing

through as a result?”


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Mesosphere’s MEDDPICC method:M (metrics): What Metrics or Measurement have you shared with your client? What addi-tional Measurements or Proof Points should be applicable to this opportunity?

E (Economic Buyer): List the Economic Buyer. Have you met with him / her?

D (Decision Criteria): Describe the Decision Criteria. How have you influenced the Decision Criteria in favour of Mesosphere?

D (Decision Process): List the Key Stake-holders involved in the Decision Process. How have you influenced the Decision Process in favour of Mesosphere?

P (Paper Process): What paperwork will be required to make the purchase happen? How has this process been documented and commu-nicated, along with the timing of each part?

I (Identified Pain): What are the biggest business and technical pains? How have you qualified these pains?

C (Champion): Who is your champion? How have you tested him / her to ensure he / she is a true champion?

C (Competition): Who is our top competition in this opportunity? Where are we strong (differentiators), and where are we weak?

“We have a phenomenal sales enablement leader here. From his previous lives, he recommended this methodology / process to give us clarity and ensure we are all talking the same language in each opportunity,” adds Hong.“And, as a result, reps understand: where am I in this deal? Is it real? Am I talking to the right person?”

For SDR-led qualification, held before an opportunity is registered, Mesosphere uses a qualification process known as CHAMP (Challenges, Authority, Money, Priority).

Challenges: What are the challenges the prospect is facing? And, can we help?Authority: This is another way of asking “who is the economic buyer?” You must ask your prospect questions that help you map out their organizational structure.

Money: Money is a critical factor. If the prospect can’t afford your product / ser-vice, they won’t buy. You must understand if they have the budget necessary.

Priority: Is the prospect determined to buy within the quarter? Or, is this a long-term plan, and the prospect is just begin-ning their research?


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A bit of advice

Clearly, sales operations teams can apply their expertise in a number of different, and critical, ways. But, warns Hong, a useful sales operations function doesn’t begin with what tools they need to implement, or what a desired outcome should be.Effective sales operations begins with one simple question: what problem are you are solving?“What are you looking to get out of this project? This is the critical question. Then, after you’ve answered that question, you can decide wheth-

er you want it in Salesforce, or in Google docs, for example,” says Hong.“It all goes back to what is relevant for your busi-ness. If you’re a small sales team, maybe Google docs suffices. What works for you should always be the driving force. It’s about having strategic conversations about a deal, or a process.”

For more on Hong’s sales operations methods, check out his interview on a recent edition of The Predictable Revenue Podcast.




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If you’re a business owner or an account executive, and you aren’t lucky enough to work in a company with a fully-staffed

sales operations team, you’re probably responsible for completing any and all pro-posals that your prospects require.

I don’t need to tell you how critical this task is. Proposals are an important pillar of the sales cycle and, if done right, can lay out a path for the completion of a success-ful project. Too often, however, proposals aren’t managed consistently – salespeople are left to manage each project as they go, without the benefit of standardized tem-plates or foundation for how to build an effective proposal.

Without that foundation, building an effec-tive proposal process never seems to make it to the top of the to-do pile.

How to nail your proposals with Mimiran’s Reuben Swartz

Reuben Swartz, Founder of Mimiran Sales Acceleration Software

“If you have a fully staffed sales ops team, you are miles ahead of many people. But, for a lot of people, there is no good training or baseline context out there for propos-als,” says Reuben Swartz, Founder of Mimiran Sales Acceleration Software, on a recent edition of The Pre-dictable Revenue Podcast.

https://predictablerevenue.com/podcast/081-how-to-nail-your-proposals-with-mimirans-reuben-swartz


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“I was a tech guy, and then I started my own firm. That meant I had to write a lot of proposals, and, I made a lot of mistakes. So,

I wrote software that would help peo-ple write proposals. In addition to that, I

spend a lot of time helping people with the process of proposals. Because there isn’t a formal infrastructure out there for every-

one to draw on, so, we copy the bad habits out there, making the process even more

difficult. If we can help people get better at this, even a little bit, it will make things so

much for more efficient for people.”

The importance of storytellingAccording to Swartz, the best place to start when designing an effective proposal (and, by extension, a proposal process) is under-standing the story you need to tell. Many businesses get this foundational piece wrong, says Swartz, because they focus

too strongly on their features and benefits, and not how those features and benefits actually work to solve a prospect’s unique problem and result in a great project.“When I joined the corporate world, I got called into the RFP process to help with tech questions. I had no training, so I would look at what others had written. And it was a lot of marketing jargon – we synergistically leverage technology to blah blah blah,” says Swartz.“At that company, we were in huge enterprise sales cycles, and there was a lot of back and forth in the process – you could get by with some of that kind of language working. But at a small firm, we didn’t have that kind of time. We didn’t have time to do lengthy discover, or flying to meet prospects. And, I had still had all of these bad habits. I sent confusing documents to people and had to explain them. I took me quite a while for me to learn that.”


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So, what did Swartz do to fix that problem? How did Swartz rid himself of confusing language, and turn his proposals into clear, persuasive documents?It was simple: he turned his attention to the customer.“I put myself in the place of the buyer. Instead of assailing them with features and benefits. I wanted to share how I could actually help them,” says Swartz.“I wanted to really learn their problem. I needed to get out of my own way. I needed to focus on the buyer.”

Swartz says that most proposals read like brochures for the company submitting it. But if the sales process was done well, he adds, and the right information was learned, there’s no need for a proposal to read as such. In fact, 95% of the work for a proposal actually happens before the proposal is even written.

“You have to nail the sales cycle. If you don’t, you can’t just magically whip up a perfect proposal. It doesn’t work like that,” says Swartz.“The goal is not to win the deal, the goal is to summarize conversations we have already had, so we can set up a successful project. That is a huge change in mindset. So, that


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means you ask different questions and be sure you understand the project. You have to understand the situation you are in, and then tell that story.”

(We recently chatted with Max Altschuler, Founder of Sales Hacker and Vice President of Marketing at Outreach, about how to understand and incorporate buyer psychology into your sales process. You can read about our discussion here, or listen to the podcast here.)

Swartz’s proposal processAlthough each proposal will, to be sure, come with uniques aspects and quirks, Swartz says there are pillars that each proposal should include.

STEP A: Book time to review the proposal. There is no point in doing any of this work if you can’t book this session. If a prospect can’t commit to a time to discuss the details of your proposal with you, they likely aren’t serious and you can save yourself some valu-able time in the process by not scrambling to produce a proposal.

STEP B: Start with a strong “Situation Sum-mary.” This section recounts why the buyer is looking for a new good or service, and what the conversation between the buyer and sell-er has covered thus far. This section sets up the rest of the journey in the proposal – the language is simple, faithfully recounts what has been talked about, and why.

STEP C: This is the section recounts the investment the seller needs to make to tackle the problem (i.e. the actual work required to handle the project). This can be as detailed as the writer chooses, but shouldn’t be over-whelming.

STEP D: This section tells the prospect what happens next (i.e payment details). Proposal writers should ensure they keep the momentum going in this section. For example, ask the prospect: “how do we get started?”Keep it simple…and make it humanFinally, remember to keep your language as simple as possible. For instance, your Terms and Conditions, a requirement for all propos-als, should be as easy to understand as possi-ble. It should be easily digestible and support the sales cycle, not slow it down.


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“It will be sent to lawyers, so don’t give them a reason to mark it up in a huge way,” says Swartz.“Make it as easy as possible to get through.”

If possible, add a short bio at the end, to reinforce the human aspect of the sale. People buy from people, so taking the opportunity to humanize the person behind the proposal can have a significant impact on the process.“Show them that they are buying from a real person. Show them that you are relatable,” says Swartz.

“People want to see that, and get to know the person they are working with.”

For more Swartz’s thoughts on proposal writing, check out the rest of his interview on The Pre-dictable Revenue Podcast.

You can find the resources mentioned in the interview or check out Reuben’s Sales for Nerds Podcast.



https://www.mimiran.com/predictable-revenue/

https://www.mimiran.com/predictable-revenue/

https://www.salesfornerds.io/

https://www.salesfornerds.io/


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Why Rambl’s Mitch Coopet believes sales and product

teams are actually two sides of the same coin

Professional salespeople, both the experienced and the novice, are, ulti-mately, hardwired to do one thing: close deals.

Sure, good salespeople have a deep bag of tactics and tricks to get them to a close, but regardless of the route they take (and a deal can go in any number of surprising

directions), the end goal of every sales cycle remains fixed.Because salespeople are trained, driven professionals, they are amongst the first hires at any early-stage company. But while revenue growth is a critical component to the success of a startup (okay, okay…the critical component), it isn’t always a dedicated

salesperson that brings on the first few customers.In fact, according to Mitch Coopet, Co-Founder and CEO of Minneapolis-based Ram-

bl, it shouldn’t be. The first customers should be closed by the founders, and those directly responsible for shaping the initial versions of the product.

“There is so much unknown, and so much variance early on. Your first few sales are really your product market thesis. You don’t know everything yet, but you have a guess. A

salesperson, though, is driven by numbers, and numbers only. So, if you set them loose, without any guard rails, they will come back with all sorts of things,” says Coopet, on a

recent edition of The Predictable Revenue Podcast.

https://predictablerevenue.com/podcast/067-the-many-lives-of-sales-why-rambls-mitch-coopet-believes-sales-and-product-teams-are-two-sides-of-the-same-coin


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“It is important, as founders and product peo-ple, not to outsource that part of the company to early. You have to have the latitude to adjust roadmaps and adjust your thinking. It takes a few customers to have any kind of product mar-ket fit. You don’t have that right away. You have to know who is a good customer for you.”And, for technical founders, adding and refin-ing sales skills is a valuable addition to one’s toolbox. Going through a few sales cycles, for instance, will teach what you can and cannot promise – a tricky negotiation sales reps face each day.

“At Code42 [the previous company Coopet co-founded, and led through two significant founding rounds], we signed a customer early on, and we did a ton of things to keep that cus-tomer happy. And, none of the things we did for that particular customer benefited our other customers down the road,” says Coopet.

“Years later, when we had well over 400 em-ployees, there were only a couple people in the company that knew everything about that par-ticular customer. But, they would still call in and ask for this and that, and it kept getting harder to support their requirements. So, the moral of the story is that chasing deals and forcing things to work doesn’t always help.”

Listen to the marketAs you set out to understand what the market thinks about your new product, it’s imperative to build in a feedback loop so any critical information learned during a sales call can be analyzed and, ultimate-ly, implemented by the product team.(Editor’s note: we recently chatted with Sean Higgins, Entrepreneur-In-Residence at Tech-stars, about growing how to grow a company from 10 to 100 customers. Read about our chat with Higgins here, or listen to the pod-cast here)

Of course, at very early stage companies, as we’ve been discussing, the information gleaned from sales calls is often being an-alyzed and implemented by a very small team, if not one person. That sounds like a lot to juggle, but that’s the job of a founder, stresses Coopet.You have to listen, find pain points, and know how your product can, or will, solve that pain.

“That feedback will help get you to product market fit,” says Coopet.

“If you don’t have it out of the gate.”

https://predictablerevenue.com/blog/test-iterate-and-scale-how-to-evolve-your-sales-process-as-you-grow-from-10-to-100-customers

https://predictablerevenue.com/podcast/064-test-iterate-and-scale-how-to-evolve-your-sales-process-as-you-grow-from-10-to-100-customers


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Tips for salespeople joining a startupWith a handful of happy (paying!) cus-tomers and a steadily improving product, it’s time to bring on someone to lead, and shape, the sales department. By any measure, this is a significant development in any early-stage company.How to hire a top-producing sales rep is a well-worn topic, discussed in-depth by sales leaders, HR executives, and successful entrepreneurs. But, just as a company interviews and evaluates its potential sales hires, so should a sales rep evaluate the company they are interview-ing with. And there are a few tell tale signs every sales rep should be on the lookout for when interviewing.

“I really do think it is important that the CEO or Founder should be able to sell the company to a sales person, and that they have sold to a handful of customers. They need to be able to

do that,” says Coopet.“They also need to be able to discuss what worked and what didn’t in those early sales scenarios. If they can’t, and they don’t know why the product has value, that’s a problem. They could be leaning on you to go figure

out the value of their product, and that is a terrible thing.”

In a situation like that, adds Coopet, it is imperative to have an upfront discussion about what you’re going to need to achieve success.“If they [the founding team] are depend-ing on you for product validation and fit, have a hard conversation with them about the latitude needed to do that. You will need it,” says Coopet.“The last thing you want to do is set your-self up to fail.”

Another thing to understand about the startup you are considering join-ing is whether the team is embarking on either a disruptive project, or a transformative one. If the company is looking to disrupt an existing market, for example, the value of their product is easier to understand. The company is, likely, utilizing its technology to 10x an existing market problem.But, if it is a transformative goal, it’s critical to get a sense of who the company is targeting, and why that target would be buying the product in question. Remember, there’s no exist-ing template for what the company is trying to do.“If they can’t do provide you with some initial target information, that’s a red flag. And if they can, test what they are saying,” says Coopet.


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“If it feels like a pretty hard story to tell – that’s another warning sign. You should be able to get that story down to one sentence.”The importance of customer supportFinally, says Coopet, sales reps should try and get a sense of the role customer support plays in the com-pany. Sales, ultimately, is all about building as many great relationships as possible – and customer support is huge part of that. It’s customer support that onboards a new cus-tomer and helps them navigate a product.But if a support team isn’t busy keeping customers happy, that could mean the product isn’t getting to market.

“Paying customers need your product to work,” says Coopet.“Nothing can go wrong.”

Admittedly, it feels counterintuitive to want customer support to be busy. No one wants their product to have problems. But, if your found-ing team has done its due diligence, engaged with the market during sales calls, and implemented the feedback they gathered, problems are going to come. Because people are using your product.

And that’s what it’s all about. Without that, growing a company, regardless of the exceptional sales-people that come onboard, is going to be even more difficult.

For more on Coopet’s thoughts on the interdependence of product and sales,

check out his interview on a recent edition of The Predictable Revenue

Podcast.

Mitch Coopet. Co-Founder and CEO of Minneapolis-based Ramb




The Sky’s the Limit: How, and Why, Sumo Finally Embraced Outbound Sales

Part of growing a business – any business – is facing, and fixing, processes that just aren’t work-

ing for your company. Sometimes, when you’re lucky, those fixes are nothing more than minor tweaks that require little debate amongst compa-ny leadership. Other times, however, significant overhauls are needed, and it takes a tough meeting to commit to change.

Nobody said it was going to be easy, right?The latter scenario is the place marketing technology Sumo found itself in just a couple years ago. Since its inception, the company had enjoyed a robust inbound funnel, and built a sales team to support the thousands of leads it had coming in.But although inbound sales propelled the company’s initial growth, Sumo is now almost completely focused on out-bound sales. In just a few short years, the company’s sales process has flipped almost entirely.“We have always been known as the inbound company, and that’s why we built and inbound sales model. It was our total focus. We were 100% inbound,” says Anton Sepetov, VP of Sales at Sumo on a recent edition of The Predictable Revenue Podcast.“But fast forward to now, and 80% – 90% of net new business is from outbound, only 10% – 20% coming from inbound. So, the tides have totally changed.”

That’s a significant about-face; most companies don’t evolve their processes quite so quickly (if ever). What, then, brought about the change?


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https://predictablerevenue.com/podcast/060-the-skys-the-limit-how-and-why-sumo-finally-embraced-outbound-sales

Too many cooksAs mentioned above, Sumo built a sales process to support the avalanche of inbound leads it received every month. That process included a team of seven SDRs and Account Executives to qualify, and ultimately close, prospects.The sales cycle was simple, and effective: SDRs would reach out to the inbound sig-nups, qualify them, and book meetings for the Account Executives. Of those prospects that made it to meetings with the AEs, 40% ended up closing.Sounds pretty good, doesn’t it?The trouble was, Sumo’s deal sizes at the time hovered between $3,000 and $5,000. And the costs of acquiring those leads via market-ing activities, and paying the sales team to handle them throughout the process, meant Sumo was often paying out more than it was taking in.“It just wasn’t cost effective. Between spending money to bring people in through inbound and having the cost of salespeople, we were losing money on that,” says Sepetov.“So, we started to think about how to make sales profitable. And we realized we had to make a hard decision: we had to focus on outbound.”

Building outboundDespite the fact that establishing an

outbound sales function seemed a clear answer to Sumo’s sales profitability

problem, implementing an effective out-bound process proved difficult at first.

Sepetov says the company’s initial outbound efforts suffered because they considered it “an experiment” and didn’t

invest the resources necessary to make it a success. For example, Sumo had a team

of SDRs and AEs working their inbound funnel, but instead of redirecting some of those team members, they decided

to hire one rep to manage the entire outbound sales cycle.

The outbound rep managed to close some deals – 30% of the calls he booked converted – but juggling closing respon-

sibilities with prospecting, ultimately, proved too much and didn’t yield the

consistent results the company needed.“We didn’t want to distract the inbound team. Of course, hindsight is 20/20, but

we never should have done that,” says Sepetov.

“We didn’t realize how long prpscteing took. There is literally not enough time in

a day for a person to do the whole funnel. You have to split the responsibilities.”


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Anton Sepetov. VP of Sales at Sumo

With that lesson learned, the Sumo team decided to make a change: they moved the inbound team over to outbound, and put marketing in charge of the inbound funnel (when an inbound lead becomes an SQL, sales is still responsible to close that lead).At first, Sepetov says, his team was hesitant. They were comfortable with inbound, and they were getting results; remember, inbound leads closed at about a 40% clip. But within a month, any hesitation the team felt evaporated. They fell in love with outbound sales.


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“We had a lot of discussion about whether or not outbound was too hard,” says Sepetov.

“But the team wants to talk to outbound cus-tomers. We strongly believe that if you can show

value, then there is little difference between inbound and outbound. Outbound should not be thought of as harder. Sure, an inbound lead knows you because they visited your site first. But if you can legitimately provide value, then

you should work together.”

That mindset, and successful transition, has been a boon to the company’s bottom line. Outbound sales now accounts for 50% of new revenue. Outbound Account Executives are now converting almost 35% of their opportunities, and SDRs are crushing their quota of at least 75 booked and held meetings per month.That’s all within just two years. “It’s very exciting,” says Sepetov.

“Just a couple of years ago, it was zero.”But despite the rapid suc-cess, Sepetov says, he is expecting continued growth from the outbound team. His goal is to help increase the team’s conversion rate to 40%, and, eventually, convince every company out there that they too need Sumo.The sky’s the limit.“With outbound, we can work with the customers we want to. There are 50 million small businesses out there that should be using Sumo, and I want them using Sumo,” says Sepetov.“When we were relying on inbound, it felt like our hands were tied. Outbound gives us control – we control our funnel. We manifest our own destiny.”

For more on Sepetov’s, and Sumo’s, transition to out-bound dominance, check out his interview on The Predict-able Revenue Podcast.




How Zendesk’s Jaimie Buss is able to forecast revenue within 1%

(at a $500 million company)

There’s detail… and then there’s detail.

We’re extremely lucky at The Pre-dictable Revenue Podcast to talk with sales pros that have built

inspiring processes that we – and hopefully our listeners – can use to help sharpen our own methods.

But this week we chatted with , about how she builds her razor sharp revenue forecasts (routinely accurate within 1%), and all of our expectations of were blown out of the water.Buss is an absolute process powerhouse. Her use of in-depth stages throughout Ze-ndesk’s sales funnel, as well as her adapt-

ed MEDDPICC qualification process, is a template we should all strive for.And the results speak for themselves.“Before implementing our processes, the fore-cast was being missed by a large percentage, maybe 25%. But, you have to be within 5% – that’s industry standard. So most quarters, we have been within 1%. For two quarters, we were within 5%, that’s not too shabby on the whole,” says Buss, during our chat on The Predictable Revenue Podcast.“But, it really comes from the team. Hands off to my team, really. It comes from them knowing the process, knowing their deals, and driving these results.”


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https://predictablerevenue.com/podcast/059-the-devils-in-the-details-how-zendesks-jaimie-buss-is-able-to-forecast-revenue-within-1-at-a-500-million-company

Stages of the sales funnelOf course, rock solid sales processes are rarely, if ever, rock solid from the start. And Zendesk was no exception to this rule. When Buss first started at the company she realized that her reps weren’t using a common language when discussing the stages in the sales funnel. For instance, Stage 2 in the sales funnel meant one thing to one rep, while Stage 3 meant some-thing entirely different to another.

THIS GAP NEEDED TO BE

FIXED – Buss had to figure out a common language that the whole sales team could use for both sales process and qualification methodology. If she was going to build a precise forecasting method, everyone would have to be on the same page.

“So, when we had a forecast call and I asked about Stage 3, we all said the same thing. That allowed me to apply probabilities to sales

stages and really asses my conver-sion rates from existing opportu-

nities based on how far along they are in the funnel,” says Buss.

“I feel so much more confident in our deals, and it gave more

confidence to our reps too. The common language has allowed us

to do that.”

So…what is that common language?It’s a sales funnel that centers

around a fixed set of stages, each with a non-negotiable customer

verifiable outcome (concrete proof from the customer that the deal can

progress along the funnel).


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Zendesk’s stages:

STAGE 1 Qualification (part 1) – Buss omits this stage from her forecast. This is general prospecting work, where no meaningful connection with a prospect has yet been made.

STAGE 1 cont’d: Qualification (part 2) – When a sales rep finds a potential deal, it lands firmly in Stage 1. The customer verifiable out-come to pass this stage is the customer attends the initial meeting and they agree to proceed to a discovery call.

STAGE 2 Discovery – This is the first stage that involves a closing rep. A general discovery discussion (are we a fit?) forms the basis of the call, with special attention paid to the stakeholders that attend. After each call, an email summary is sent, con-sisting of what the agreed upon next steps will be, and a summary of what the Zendesk reps have learnt thus far. Finally, the customer verifi-able outcome is that the prospect attended the call, and has agreed to get the right people on the demo coming up.


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STAGE 3 Solution Review – This is a critical step. The solution review is when the Zendesk rep performs the demo, and gathers any of the technical requirements the prospect needs. That doesn’t necessarily mean it’s a technical win for Zendesk, but the rep, at least, understands all of the technical requirements involved in the deal. The customer verifiable outcome is that “doing nothing” is off the table (the customer has confirmed they will be moving forward with a software solution of some kind). The way Zendesk confirms this is by quantifying that doing nothing is more expen-sive than implementing a new tool.

STAGE 4 Solution Validation – At this stage, Zendesk has confirmed they can meet the technical criteria, and they have gath-ered a full picture of the paper process involved in closing the deal. For instance, who needs to sign? Is there an order of operations that the signing process needs to follow? And, does the customer need to issue a PO? The customer verifiable outcome is that Zendesk understands

everyone that needs to be involved the deal (the aforementioned paper process).

STAGE 5 Verbal Contracting – This is, simply put, the contract negotiation phase.Typically, there is an agreement on price, but there may be concessions that need to be dealt with as well. The customer verifiable outcome is a signed service order, and a signed services agreement, if they’ve negotiated one. If there is a statement of work, then that needs to be signed as well.

STAGE 6 Finance Review – Finance takes over at this point, and reviews everything to make sure there are no omissions. If something needs to be reworked, finance will send it back to sales at this point.

STAGE 7 Finance Final Round – This stage isn’t done with sales at all; finance just checks all the boxes, ensuring the docu-mentation is accurate.

MEDPICC Qualification (this applies to all deals over $12,000 ARR. Deals below this threshold aren’t subject to these constraints)

In case you thought those funnel stages weren’t quite thorough enough, Buss also uses an in-depth qualification method to score Zendesk’s opportunities and highlight the health of each pending deal.


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Jaimie Buss.VP of North American Sales at Zendesk

“What you need on top of the sales process is a qualification methodology because qualification runs through all of this. The sales process is all about the customer verifiable outcome. They’ve told us we’ve won, or they’ve told us we won technically,” says Buss.“But, I am a process oriented individual. And in a high paced, transactional environment, I felt the team needed a way of scoring their opps to show how qualified they are. Opportunities aren’t all the same, of course.”

MEDDPICC stages (shown here out of order, the order of the acronym isn’t important):

Metrics – this step is all about how Ze-ndesk quantifies success for the customer. For example, what are the metrics their customers are gathering that they want to change? Is it response time? Or, is it resolu-tion time, or customer satisfaction? These numbers form Zendesk’s ‘as is’ statement about the customer. Then, Zendesk asks what the customer wants those metrics to be. Those desired metrics are important – they become an anchor along the sales process. If possible, Zendesk will quantify what those desired metrics will mean to the prospect.

Identified Pain (this is a critical step) this is very closely related to the metrics step. An easy way to quantify this is to highlight how many SLAs the prospect is

missing on a monthly basis, and what the cost of missing them is. This is a critical piece of qualification – if Zendesk can high-light the cost of doing business ‘as is’ they have a better chance at winning the deal.Zendesk reps also score this step in Sales-force: a score of 0 means they don’t know what the pain is. A score of 1 means the rep has uncovered the pain, but can’t yet quantify it. Finally, a score of 2 means the rep has identified the pain and quantified it so the customer agrees that ‘doing nothing’ is no longer an option.

Economic buyer (this is another critical

step) – the economic buyer is the person that owns a budget and, if they choose, can move money around to make a purchase. For example, they can hold off hiring for the quarter, which frees up enough money for me to make a SaaS purchase.Zendesk also scores this in Salesforce: a score of 0 means they don’t know the eco-


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nomic buyer. A score of 1 means they know who the economic buyer is, but doesn’t have a relationship with them. Finally, a score of 2 means they have built a relation-ship with the economic buyer.

Decision Criteria – this is all about the technical requirements needed to win the deal. Zendesk reps are required to know what they do well that the competition can’t do, as well as what the competition does well. And, of course, they also need to know where they overlap with the compe-tition.Zendesk scores this in Salesforce as such: a score of 0 means they don’t know their cri-teria. A score of 1 means they have mapped the technical requirements out, but haven’t met them all. A score of 2 means they have mapped out the requirements, and con-firmed with the client that they can meet them all.

Decision Process – this step requires an understanding of all the stakeholders involved. For instance, there may be hidden business lines that could be involved or im-pacted by implementing their tool. Zendesk needs to know that.Zendesk scores this in Salesforce as such: a score of 0 means they don’t yet know all of

the stakeholders. A score of 1 means they understand the process, and who all the stakeholders are. Finally, a score of 2 means they know all of the criteria, and they’ve proven they can meet them.

Paper process – this step requires an understanding of all of the signed contracts needed to win the deal. For example, who are all the people needed to sign? And, what is the departmental sequence re-quired for the contract signing?Zendesk scores this in Salesforce as such: a score of 0 means the rep doesn’t know what needs to be signed (highly unlikely). A score of 1 means the rep knows everything that has to be signed. And, finally, a score of 2 means the rep knows everything that has to be signed, the order in which they need to be signed, and they can closely predict the closing date.

Champion (this is an important step) – Zendesk defines a champion as: someone who has power and influence, and something to gain from the deal. The champion may not be able to move money like an economic buyer, the champion is willing to get the deal in front of one and pitch it.Zendesk scores this in Salesforce as such: a score of 0 means they don’t have a champion.


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A score of 1 means the rep believes they have a champion, but has not tested that person. Finally, a score of 2 means the rep has a champion, and has tested their willingness to get the deal in front of an economic buyer.

Competition – this is a great way to test the champion. For example, Zendesk reps will always try to get the champion to dis-close who they are up against. Knowing who the competition is helps Zendesk set the fo-cus of the conversation (remember, Zendesk reps know the strengths and weaknesses of their competition intimately).Zendesk scores this in Salesforce as such: a score of 0 means they don’t know who the

competition is. A score of 1 means the rep suspects who the competition is, based on inference. A score of 2 means the rep has been told who they are up againstBased on the scores attributed to each step, Salesforce will add the results up for Buss, giving her a concrete look at the health of each opportunity.What did we tell you? There’s detail…and then there’s detail.

For more on Buss’ forecasting methods, in particular how she structures her sales funnel and designs her qualification process, check out her interview on a recent edition of The Predictable Revenue Podcast.


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