Prime Future 115: Building the (sales) machine as you fly


Let’s talk about building out a sales capability within a startup. This is so tricky because, by definition, you are building the sales process & capability from a blank piece of paper. Just straight up building the machine as you fly it.

Below is a laundry list of things I’ve learned about building out a sales capability from my own experience as a sales rep, as a founder (early sales can’t be outsourced), and as head of commercial scaling up a SaaS sales org…and from great mentors and other resources.

Some of the below is from my playbook, and admittedly a lot of this is what I wish had been in my playbook sooner….aka things I’ve learned by making all.the.mistakes. And the thing about the art & science of sales is that the more you learn the more you realize how little you know.

The caveat to the list below is that everything in sales is contextual; none of these will work all of the time but most of them will work some of the time, depending on the context.

Building a sales organization is about building a capability, a machine that will repeatedly produce predictable results. A constantly evolving machine that needs constant refining.

My overarching goal in building a sales machine is to build in ways to accelerate learning velocity – as individuals, as a team, and as an organization.

You can get as complex as your heart desires, but sales does not have to be complicated. Basic frameworks can be super helpful. These range from hiring to training to sales meeting structure to sales process.

(1) “Tell me about something you’ve recently geeked out about learning.”

I will forever and always believe that curiosity is the single best predictor of success in a salesperson. I want to know that a salesperson is intellectually curious about…anything. I always ask this question in the hiring process. If they aren’t curious about non-customer things, they are unlikely to be curious about their customers.

(2) “Tell me about a recent example where you received feedback, implemented it, and what the outcome was.”

This is another interview question. I will forever and always believe that the appetite to seek feedback, hear feedback, and implement feedback is another predictor of success in a salesperson. Too arrogant or set in their ways or closed-minded to change? Hard pass. The ability to take feedback is a proxy for the rate of learning. And by taking feedback, I don’t just mean from their manager, I mean from their peers and much more importantly, from the market.

(3) Red flag if customer facing candidates don’t negotiate their own comp.

If I’m hiring someone for a commercial role in which they are responsible for selling value to customers in exchange for dollars, I fully expect them to negotiate their own comp package. Why would I expect them to be able to ask customers for more money on behalf of the company if they can’t ask for more money on behalf of themselves?

(4) Hire salespeople in pairs.

Especially early in the commercialization of a new product or service, if you hire 1 person and they don’t make progress then you don’t really know if it’s the person or if it’s the product, the pricing model, etc. But if you hire 2 people at the same time and 1 is successful and the other is not, then you have a better idea. (Though if you hire 2 reps and neither is successful, you need to take a good look at the product & go to market because maybe it’s not ready for prime time!)

(5) Be very very clear whether your company needs farmers or hunters.

Farmers are the sales reps that have the crucial skills of maintaining relationships, over years or sometimes decades. Hunters are the sales reps that take you from 0 customers in a market or region to your first 10 customers. If you are an upstart, by definition you need hunters first. Of course, there are exceptions, but in general, farmers don’t make very good hunters and hunters don’t make very good farmers. Resource accordingly.

(6) Don’t over-index for someone that looks/sounds/acts like your customer.

This is common in agtech companies, particularly with founders who are not from ag and have maybe struggled a bit to build credibility with early customers. You want your customers to accept your salespeople so you hire people who look and act and sound like your typical customer. The problem is this only works if those people have the capabilities to go with the persona. If not, you could be burning valuable dollars and time in a mis-hire.

(7) Practice like you play; sales role plays make everyone better.

Most anyone who’s been in sales has been forced to role-play sales scenarios and likely hates doing so. But sales role plays are really effective ways to practice how you’ll play in the big game moments, and create opportunities for peers to coach each other up…and since anytime we teach we learn more ourselves, there’s this powerful acceleration that happens for the entire team simultaneously.

Role plays don’t have to be extensive, it can be as simple as 10-minute drills in a team Zoom call where a prompt gets thrown out “You’re in the 2nd meeting with x prospect who has y objections, how do you handle those objections?” 5 minutes to role-play, 5 minutes of peer feedback and we’re on to the next person.

These are so valuable because they force you to go from ‘here’s what I would say’ to ‘let me practice saying it’….which is way harder. And maybe it leads to a team brainstorming about how to handle some scenario that continues to come up again and again…..its’s all about accelerating learning velocityAnd it only works if the team is filled with relentlessly curious individuals who have the humble confidence to seek & accept feedback for the purpose of getting better faster.

(8) Planning matters, even for experienced teams. The best sales meetings are usually the best prepared.

Even if all you do is jot down at the top of a note page the 1-2 objectives of the meeting, and the 2-3 key questions you’d like to ask to accelerate the sales process. Its really easy to get lazy and skip this planning step, which often ends up being disrespectful to the prospective customer and disadvantageous for the salesperson. This is also one of those sales organization cultural things – either it’s expected that we as a team are planners or it’s accepted that we wing it.

(9) Respect your customer’s intelligence.

I reeeeeally hate it when sales people use superfluous adjectives to sell me on something. Don’t tell me what to think about your product. Present me the information or the data or the case. I can make up my own mind and reach my own conclusions, thank you very much. It’s as simple as reframing things from “x feature is so awesome because it lets you do y which is really fantastic” to “x feature allows you to y, how could you imagine that capability impacting your process?” Too many positive adjectives makes me cringe at best, distrustful at worst….I don’t think I’m alone in that.

(10) Be aware of how much time you talk in the conversation.

It’s hard to learn and uncover what’s important to your customer if you’re sucking up all the oxygen in the conversation. Pay attention to how much of the conversation are you talking or the prospect talking. Are you taking up 90% of the air time? 80%? If so, maybe don’t act surprised when the prospect ghosts you. Side note – maybe this is a good awareness exercise for personal relationships as well… Also, the caveat here is that it depends on the nature of the meeting, where you are in the process, how well you know the prospect, how much trust has been established, the prospect’s conversation style, etc. But the general principle still holds.

Sales Process:

I was trained in consultative selling skills as a brand new baby sales rep and I believe in it so wholeheartedly for almost any type of sales but especially for products and services that involve complexity and/or ambiguity and/or complex value propositions. It’s all about understanding the customer’s context to more effectively solve it, aka identifying the right customers and customer situations to create actual value.

The foundation of a sales process is how we run individual sales meetings which then gets layered into the larger sales strategy, and the skeleton of those meetings should usually be the same regardless of the content, beginning with a stated purpose of the meeting.

(1) “The purpose of this meeting is….”

Most meetings are a waste of time because the purpose is not clear, so state it up front. What are we all going to get out of this time, especially the prospective customer?

I love the framework of Purpose, Benefit, Check:

  • Purpose – state the reason for the meeting
  • Benefit – state the benefit to the other person(s)
  • Check – confirm everyone is aligned about the use of time

So it sounds something like this, “The purpose of this meeting is to explore x so that we can make a decision about y. What else would you like to accomplish in our time today?”

My hypothesis is that 30% of meetings would become emails, and 70% of meetings would be more productive if every meeting started with “the purpose of this meeting is….”

Having a clear Purpose-Benefit-Check sets the tone of the entire meeting. Having this written down ahead of time increases the odds that it will come out how you want it to instead of a jumble of words.

(2) Advance the meeting on purpose.

You know what the purpose of the meeting is because you’ve stated it and everyone agreed to it. Now be thoughtful about how you might get there!

One part of advancing the meeting is asking smart, well-worded questions that expand & accelerate the conversation…

(3) Level up from close-ended to open-ended questions.

Only use yes/no questions rarely and on purpose. 99% of the time an open-ended question will be a higher-yielding question. There’s a big difference between “is your feed conversion where you want it to be?” and “what’s your philosophy for managing feed conversion?

Exercise: have a peer join you in a meeting and keep count of how many yes/no questions you ask, and how many open-ended questions you ask. Chances are you’re asking more close-ended questions than you realize, or would like…most of us are. It takes awareness and practice to build the muscle of asking quality questions.

(4) Level up from open-ended to high gain questions.

There are open-ended questions that open up a conversation, and then there are high-gain questions that lead to magic. Here are some examples:

  • What are your top 3 issues managing feed conversion today?
  • If you had to choose 1 of those issues to solve, and you had an unlimited budget, how would you tackle it?
  • If you could solve that issue, what would it mean for your business? Your budgeting? Your operations? Your board of directors?

The catch here is that you only get to ask so many high-gain questions in each meeting or else it feels like an interview. And in my experience, most people do not think of good high-gain questions on the fly. So this is REALLY a place to plan ahead.

(5) So much momentum gets lost in sales processes because the ball gets dropped in the follow-up.

Close the meeting with a summary and next steps. Then send an email with a summary and the next steps. Then do the next steps.

(6) In most B2B contexts, unpaid pilots = uncommitted customers that are hard to convert to paying customers.

It’s not about the revenue, it’s about the psychology of the user: what's free doesn't feel as valuable as what we've paid for.

(7) Quantify the pipeline as early as possible.

This lets you identify trends around bottlenecks and what’s working or not working. However rough the data is, however limited the systems are….even estimates are better than nothing. This can be as simple as:

  • Leads
  • Qualified Leads
  • Demo
  • Proposal submitted
  • Contract signed

(8) Create shared language on the team.

Having 1-2 anchor books that every new hire reads and that we refer back to as a sales org can be really helpful in anchoring everyone to the same language and ideas…another way to accelerate learning velocity. Here are a few of my favorite resources:

Ok that was a lot and it barely scratches the surface, but I hope you found at least 1 helpful nugget.

The rebuttal to some of this is that it sounds robotic and formulaic at first glance, but that’s why you practice and iterate and make it your own until it is completely natural and genuinely fits your approach.

Really effective sales people have really effective systems and processes, so do really effective sales organizations.

It’s like the James Clear quote:

You do not rise to the level of your goals. You fall to the level of your systems. Your goal is your desired outcome. Your system is the collection of daily habits that will get you there.”

A huge part of the fun in building out a sales capability is stealing from existing playbooks what you can, modifying where you need to, and creating what’s missing for your specific customer/product/market….all part of building the sales machine as you fly 😉

What are your 1-2 favorite sales principles?

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