lesson 7

Train and Retain Your Reps

The more you train your reps, the more they’ll succeed. The more they succeed, the more likely they are to stick around and train others, in a virtuous cycle. The challenge is, most sales reps tend to be resistant to change (recall Lesson 3). Even when their version of the pitch wanders away from the core messaging, they’ll want to keep doing it that way because that’s what they think works. Most don’t love having to retrain.

But if you aren’t creating a culture of continuous learning and re-learning, the sales machine can slow to a grind, and it won’t respond to the changes in the market or business.

Consider one public company that spent twenty years successfully selling an email security product, then acquired several other companies to build one unified suite of tools. No matter how much their product marketing organization tried to pitch the new vision—one unified suite—salespeople were so used to selling the old product they couldn’t think beyond it. Retraining wasn’t a skill they’d ever had to practice. It wasn’t part of their culture. The switch became a long-running battle the sales organization resisted, and the new products didn’t sell. 

In this chapter, we’ll explore how to train and retain your salespeople to create a culture that continues to adapt.

What you’ll learn

  • How to help reps master storytelling
  • Advice on sales rep learning styles
  • Communications to send
  • How to sharpen your hiring criteria
  • The not-so-secret key to retention
  • Plus, access free training content for popular tools

Give reps exposure to the company’s chief storytellers

Nothing helps sales reps learn like listening to, reading, and watching founders and executives. Those individuals know what the market needs and the story to convey it. Back to our point in Lesson 3 about every level of salesperson thinking on a different time horizon, your executives have the best grasp on the succinct, global pitch. It’s more than just the sales leader’s story. It’s why the company exists. Salespeople need exposure to that, repeatedly.

Early on, that exposure occurs naturally. As you grow, it becomes harder and harder to convey. You may think reps get it from one or two interactions, but that’s not enough—they need many sessions. Even if they start to pick up the story once, they’ll adapt it to their purposes, the message will drift, and they’ll need a refresh. With each refresh, you’ll improve the discovery calls, pitches, and demos of all involved. 

To distribute those chief storytellers’ stories:

  • Record and distribute their talks
  • Ask each founder to record a 20-minute interview on the company’s origin
  • Record your pitch certifications and make the best ones available

“Time in seat matters. It’s a value of being early at a company and having some leash. You get to spend time with everybody, from engineers to the CEO to the marketers in a lot of freaking calls and you learn. Going into a company at quasi-scale is in some cases harder because your clock starts immediately. You don’t get that opportunity to listen.” – Scott Edmonds, CRO at Syncari

“At Marketo, it clicked for me when the CEO gathered 20 or 30 of us and gave the pitch he was using to raise our series B. I’ll date myself, but I had a tape recorder, like a journalist. When I went into my pitch certification, I got demolished. I was frustrated. I went out for lunch, got a slice of pizza, sat on my laptop, plugged in my headphones, listened to the recording, and typed it out verbatim. I deleted it. I typed it out again. I deleted it. I typed it out again. That’s when the story finally clicked. I understood the deeper nuances. From there it made sense.” – Scott Edmonds, CRO at Syncari

Every rep has their own learning preference

What works for one may not work for all. Offer a mixture of media so there’s a bit of something for everyone. While you probably don’t have the resources to turn every video into an article, or every audio recording into a deck, switch it up so no one learner preference is ever left out. Even better, survey your reps to figure out how they prefer to learn.

  • For visual learners, use videos and decks
  • For auditory learners, use audio or video
  • For kinesthetic learners, use role plays
  • For reading/writing learners, use articles and books

“Everybody learns differently and also some people are more interested in learning than others. To me, if someone is uninterested in learning, it usually indicates they’ll struggle in sales. And some people are just natural learners who don’t have to study as hard. I don’t need everybody to learn the same way. In fact, I value creativity and try to hire people who think differently. As long as they have that kernel of a story right, they can get there any way they like.” – Scott Edmonds, CRO at Syncari

Ongoing tests and certifications serve multiple purposes

Certifications ensure that all salespeople are reaching a minimum baseline, reflect well upon the company, and are prepared to own their success. But the mere presence of testing also reinforces the idea that training and testing are part of the job, and inspires people to always be in some phase of educating themselves. 

Establish a product and market information pipeline 

As long as things change—and they will change as long as you’re in business (see Lesson 3)—you will be reskilling salespeople. It becomes even more important the larger the team grows. At a certain span of control (generally, more than five direct reports), managers have a less good grasp on who’s doing well in what areas. 

Consistent, non-optional trainings ensure you’re identifying and documenting where each person can improve, so you can focus your assistance.

Ways you can communicate product updates:

Twice per month
ProgramRevenue team newsletter
What it coversThe newsletter itself
Product updates
CRM/tool updates
Competitive intel
Spiff reminders
Marketing campaigns
Owner (can delegate)You
Product marketing
Product marketing
Once per month
Program2hr sales meeting
What it coversThe meeting itself
Narrative updates
Strategy updates
Marketing updates
Owner (can delegate)You
VP of sales
ProgramA list of internal experts
What it coversWhich experts are responsible for answering which questions, plus how to reach them
Owner (can delegate)You
Pitch competitions
What it coversChallenge reps to master a new message and offer a prize for the best pitches according to a panel.
Owner (can delegate)You, sales leaders

“In startups, stuff changes every six months. Sometimes faster. Your product changes. Pricing changes. Competitive plays change. The landscape changes. There’s this ramp period to get you good at the core. But even somebody who’s been here for two years, we’ve got to run new certs and new training. The ongoing stuff is hard because it’s difficult to know exactly who’s good at what at any given point. Ongoing tests and certifications are very important to catch that.” – Scott Edmonds, CRO at Syncari

Welcome the mess

To retain reps, you have to train them. To train them, you need an honest view of how they’re doing. Many sales organizations fail to create that. They stack rank the sales reps, push them to commit moonshot deals, punish their mistakes, and generally teach them that to succeed, they must conceal some things. But as we covered in Lesson 3, highly successful sales organizations tend to have the opposite culture. You need to help your sales leaders and managers get accurate information, and that starts with rewarding reps for revealing their mess.

The simplest thing you can do is be excited and non-judgmental when they bring you inconvenient problems. Encourage your sales managers and leaders to adopt the same stance. Business strategist and author Jocko Willink recommends this method: Respond to all news, good or bad, with the word, “Good.” Just learned the deal is on life support? Good. The stakeholder left mid-evaluation? Good. We promised something we can’t deliver? Good. We’re going to win no matter what? Good. This reinforces that it’s always just a puzzle and you’re all in it together. 

“You have to help your sales managers learn to embrace their inner Marie Kondo feeling of, ‘I love mess.’ You want your reps to bring you things that aren’t going well. There’s no judgment, we’re in this mess together. But you need to share that with me so we have all the same information about the health of our opportunities. For example, not having done certain activities, or not meeting certain exit criteria. Your feelings as an AE and your sentiment about your opportunities are valid, but we as a team need to understand why you aren’t confident about moving a deal forward. It’s likely because we’re missing important data (e.g. MEDDPICC), and you have to let me know so that we can meet in the middle and make it work.” – Rachel Ha’o, Global Sales Enablement at Iterable

Use your top reps to develop a sales rep hiring persona

Applications are barriers. Phone interviews are barriers. Everything in your interview process is a type of barrier between candidates and getting the job. Whatever barriers you create, be sure they’re actually helping you select the right people. Often, hiring managers rely on old practices that serve no purpose other than to weed out great-fit candidates. 

For example, consider the college degree requirement. Does having a college degree make someone a better sales rep? The jury’s out on that one. In which case, why turn away every potential non-degreed candidate if you don’t actually know that’s helping you? In fact, if everyone else is turning away non-degreed candidates, and you’re the only one hiring them, doesn’t that mean you have access to a pool of skilled but overlooked talent? 

Tech companies have learned this lesson in hiring developers. For a long time, developers were required to solve problems on a whiteboard before a slate of interviewers. It ends up, that’s a pretty stressful test. Many developers felt nervous about it, and underperformed. These companies were disqualifying right-fit candidates for no particular reason.

To know what barriers your team should create, work with sales leaders to build a sales rep hiring persona. Base that persona on conversations with sales managers and with top reps. What characteristics do they tend to have? What do they share in common? Write it down and devise tests that actually select for those sorts of individuals. 

Desired characteristic A test you can run
Detail-orientedHide a secret instruction in the job description.
For example, at the end of the application, in the fine print, place the text: “If you read this, put a “Moyai” emoji at the start of your application subject line. We will not consider applications unless they begin that way.”

Ignore all applications that don’t begin with 🗿.
CuriousIn the job description, tell them you can’t tell them everything unless they sign an NDA. Or mention a step in the hiring process that doesn’t quite make sense. In the interview, see whether they bring this up and want to know, or whether they tried to figure it out on their own.
CreativeEncourage them to use alternative media in the application, like video. Leave these instructions vague and see what they do.
Self-starterAsk them how they’ll make the most of their territory. Use a thought experiment: You’ve just been appointed CEO of their territory. You get a budget and can do anything. How would you make the most of it?
PersistentPolitely ignore their application.
Adapts on the flyInterrupt their interview. Have the second interviewer arrive early, interrupt the first, and tell them that they’re needed elsewhere. The second interviewer then sits down, changes the subject, and sees how the rep reacts.

“It’s important to have an ideal persona for the type of rep you’re trying to hire. That persona is essentially my theory of who’s going to be successful at this. I’ll veer outside of it if I feel like it, but it’s good to have a thesis. It could include anything. Everything from deal size to ancillary product knowledge to style to career stage to the number of deals closed per year to startup experience.” – Scott Edmonds, CRO at Syncari

In interviews, be candid about what they’re getting into

In most hiring cycles, candidates and managers both sell each other. Try to limit that on both sides. A rep who feels they’ve been deceived about the opportunity will be much less happy than they would be in the same role, but where they were informed. Being radically candid can also be a useful filter. Prospective hires that are scared away by a little messiness probably aren’t the people you need right now. The right reps will see it as an opportunity. 

“When you get into a job and it’s not what you were told it was going to be, that sucks for everybody. I would try to be as honest as I can and frankly try to scare people. If they’re still standing, then maybe it’s a good fit.” – Scott Edmonds, CRO at Syncari

The secret to retention? Ensure reps are making money

And that they see a path to making more money in the future. Reps who are perfectly content but don’t see how they’re going to inherit a better territory, develop their skills, or move up, are liable to be poached. 

Similarly, ensure there’s a career path, especially for sales development reps, and that it’s well-communicated. Like a convoluted compensation plan, a career path doesn’t work if nobody knows it exists. It also helps to develop a strong, positive culture where they feel supported, and they get the feedback they need to feel like they’re effective at what they do (see Lesson 1). 

Together, these constitute the four “Cs” of retention: compensation, career, culture, and confidence. 

“Ensure they’re making money. Pretty simple. All of us, no matter what we’re doing in sales, want to feel like we’re good at our jobs. Usually that’s pretty binary. We’re closing deals. That shows up in the paycheck. Everybody’s motivated slightly differently, but that’s the denominator.  Find a way to help somebody who’s at their 80% of plan get to 100%, and the person at 100% get them to 115%. People who succeed tend to stick around.” – Scott Edmonds, CRO at Syncari

“You have to invest in your people. Most SDRs leave before they ever take an account executive role because someone else offers it faster. And that knowledge goes with them.” – Mollie Bodensteiner, Global Revenue Operations Leader at Deel

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Table of contents


Design Your Sales Playbook


Build an Airtight Onboarding Flow


Managing Change


Selecting Sales Tech


Get the Most from Your Tech


Build a Capacity Planning Growth Model


Train and Retain Your Reps


Course Recap


You’ve finished Lesson 7 in Spekit’s course, Helping Sales Scale.


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