lesson 3

Managing Change

When Bob Dylan wrote “Times They Are A-Changin’” he wasn’t talking about sales organizations or startups, but he might as well have been. There’s something hauntingly prophetic about the lyrics. They remind us that whoever is ahead now can just as easily fall behind, and that if you slow down, you may get trampled.

From the moment you begin your RevOps or sales enablement role until the moment you leave, the sales organization will be changing. How you manage that change—how you help others survive and capitalize upon it—is how you’ll succeed. 

In this chapter, we’ll share change management advice from sales leaders who’ve guided revenue organizations through every stage of startup life. While you aren’t exactly their boss, you still have to manage up and help those leaders change too.

Perhaps Dylan put it best: Come senators, congressmen / please heed the call / don’t block up the doorway / don’t stand in the hall / for he that gets hurt / will be he who has stalled. 

For the sales org is a-changin’.

What you’ll learn

  • How to prepare everyone for change
  • A change management manifesto
  • How to productively experiment
  • Plus, a change management checklist template

Why do sales teams change so much?

Because life is change. Markets emerge, fads erupt, and niche ideas go mainstream. IT teams adopt servers then abandon them for the cloud. Overnight, marketers only seem interested in software that claims to be “account-based.” Every business must adapt to change, and as the tip of the revenue team, sales must adapt the fastest.

Build a team that can handle the coming change

Despite the certainty of change, salespeople tend to be among some of the most risk-averse people in business. Their income is perpetually at risk and when they accumulate habits, practices, decks, and talk tracks that help them close deals, they want those things to remain fixed so they can continue to exploit their advantage. But they’ll need to be open to change, and part of your success is in how you help them adapt. 

It’s also partly in how you hire. Everyone has different appetites for risk and change. If early on, you can hire people who welcome change, you’ll have a more nimble sales organization. 

As your business grows, you’ll be hiring three waves of salespeople: 

  • First-wave go-getters: These people are happy selling with little more than a phone. They exhibit an extreme tolerance for uncertainty, see opportunity in chaos, and are entirely self-motivated.
  • Second-wave process setters: These individuals require structure, examples of successful customer implementations, and some procedural precedent to build off of. But provided that, they excel at creating a sales machine, documenting what works, explaining it, and doing whatever jobs need to be done.
  • Third-wave maximizers: These individuals demand direction, training, and structured feedback. But given that, they excel at mastering processes and repeating their wins.

If you hire the right salespeople at the wrong time, they tend to struggle. First-wave go-getters will chafe at reviews and certifications. Third-wave maximizers will feel like they’re drowning if not provided formalized training and support. Hire the right people for the degree of change they’ll be facing, and tailor your hiring process to help tease out their change tolerance.

Those waves may correspond to the overall maturity of the business, but they might also correspond to the maturity of a given team. If you’ve just launched your first vertical-specific sales team, you might want first-wave go-getters.

Change management is won or lost on who you hire, and into what environment.

Suresh Khanna
| Co-Founder of Pieces

Develop strong ties to sales leaders

Nothing will carry you through difficult times like sales managers and directors who know, like, and trust you. Befriend them. Be visible and vocal about how you can help them achieve their goals like onboarding reps, finding more leads, resolving territorial disputes, and hiring talent. Cultivate those relationships in the good times so they carry you through the bad. 


  • Schedule time to hear their priorities. Follow up with how you can support each point (or can’t). Deliver value in that meeting—you want to anchor the idea that this is a mutually beneficial partnership.
  • Schedule recurring check-ins where you come prepared to deliver things they find valuable. If you don’t have something, cancel the meeting and give them the time back.
  • Look for opportunities to do favors.

Create a culture where people share problems

Wherever people feel uncomfortable delivering bad news, bad things follow. On a small scale, you get politicking. On a medium scale, you get an office emperor who has no clothes. On a grand scale, you get disasters like the 2013 Asiana Airlines crash where investigators found that the co-pilot was aware they were in danger but did not speak up because he felt inhibited by cultural norms.

Leaders cannot solve problems they don’t know about. The best (and perhaps only) way to encourage a culture of candid sharing is for sales leadership to model it. They must openly share what’s not working, especially if it’s something they’ve done. And they must reward people when they constructively share their problems.

The more ingrained an existing sales culture of secrecy is, the longer it’ll take to fix, and the more overtly your sales leaders will have to share to overcome it.

“I learned this the hard way coming up the ranks at Google. We didn’t talk about problems in the open. Talkers were considered complainers. But then they’d roll out solutions where you’d think, ‘What the hell? Who came up with that?’ Or, management would change things and not explain why, and it’d make things worse, but you didn’t feel you could tell anybody.” – Suresh Khanna, Co-Founder of Pieces

“You don’t have to come to me with a solution. Solutions can be multivariate and complex. They are hard. If you have a solution, great. Share it. But let’s focus on the problem. Encouraging this mindset can detach the reps from emotion around the solution, because they might not necessarily be the right person to determine the fix. They might be, but maybe not. I want them to bring me problems.” – Suresh Khanna,Co-Founder of Pieces

“Don’t bring me the solution, don’t bring the tool you want. Bring me the problem and let me fix it and give me money to do it right and not cheap out.” – Andy Mowat, CEO and Co-Founder of Gated

Suresh Khanna’s change management manifesto

“Have sales leadership set the example and publish a manifesto like the following. It tells everyone that you value accurate information because it’ll help you solve their problems. This creates a system that rewards open sharing. 

Work culture manifesto:

  • We talk about our problems in the open. There are no taboos. To solve the problem, we must know everything.
  • We share ideas. Everyone has a voice.
  • We have a bias for action. If you make a decision, explain it.
  • We exist in a neverending feedback loop. We constantly reevaluate to fix or optimize.
  • There is no room for ego. You should be excited to share failures. It means we learned.

If all this is true, you can ask every person in the organization to be a player, not a hater. Encourage them to, instead of sitting at their desk and complaining, share the problem with leadership, trust that they were heard, and return to work.” – Suresh Khanna,Co-Founder of Pieces

Help sales leaders craft their “change is coming” speech

Normalize change. In your communications, help account executives see that to be successful, they have to become masters of change. In chaos is opportunity. Are they going to be victims or will they bend it to their advantage? 

As Dylan put it, the slow one now / will later be fast / as the present now will later be past / the old order is rapidly fadin’. The truth is, your company’s “old order” is always fading. It’s always being replaced by something new. That’s why you must let your top performers know they are responsible for being a positive force for change. Add a checkbox to your team’s sales reviews asking whether they’ve been a promoter of changes, or a detractor.

“When I came in as CRO at AdRoll, I said to people, ‘We are going to change. We are going to change constantly. Because if we don’t change, we’re going to die. The things that work at 25 people won’t work at 50. Then it’ll break at 100. And by the time it’s broken, it’s too late. So everybody needs to get into the mindset that change is normal. Who you sit next to, who your boss is, what territory you have, how many leads you can put in Salesforce, the commission systems. It all must change.” – Suresh Khanna,Co-Founder of Pieces

“I started out as the first account executive at Marketo. There was no messaging, there was no playbook. There was barely a product. In fact, interestingly, we had a product that didn’t work particularly well, which they scrapped. Three months later, we launched what’s now their flagship marketing automation product, and I started selling that.” – Scott Edmonds, CRO at Syncari

There’s no room for stupid rules

Managers and reps need a venue for fair arbitration. If you’re too strict about holding everyone accountable to fixed rules in an environment that’s rapidly changing, there will be times when the rules work against your top performers and most creative reps. Remind leadership that the most important thing in these instances is to respect the spirit of the law, not just its word, and reward what drives fairly gotten revenue.

“Early in my career, I ran a new business sales team. At one point, sales operations decided that we, the hunting team, could no longer sell to anyone who had spent even a penny on our product in the last two years, because technically, they were not ‘new business.’ Not long after, my team won a seven-figure deal with a client who, it turns out, had spent a tiny amount of money on a test the year before. Finance said ‘Nope. That’s not new business,” and we didn’t get credit. Everyone on the team was upset. And you have to ask yourself, what problem were they trying to solve with that rule? Everyone was worse off with that policy, from the client to the sales team to the company.” – Suresh Khanna,Co-Founder of Pieces

Know your audience’s time horizon

Tailor your communications based on the relative time horizon of those you’re talking to. Account executives tend to be short-sighted and need the least advance notice. The more senior people get, the more notice they need.  

“Everyone sees things from a different time horizon. The AE is thinking about how to have a great month. Managers are thinking about having a quarter. Directors and VPs want a great year, and the CRO is thinking, “I’ve got to hit next year if I’m trying to triple, triple, double, double. I need the bodies.” – Suresh Khanna,Co-Founder of Pieces

To productively experiment, launch a sales advisory board

All that change talk aside, no matter how much you prep salespeople, you do need to guarantee some certainty on a near-to-medium time horizon. Salespeople can’t throw themselves into developing a territory if they know it’ll just be ripped away. Sales managers can’t earn their team’s respect if the things they promise evaporate. Prepare everyone for change, but minimize unnecessary change as much as possible—and that includes changing things in the CRM.

To test changes and prevent blowback, launch what’s known as an informal sales advisory board. These are your most change-tolerant and forward-thinking sales managers and reps who are willing to play guinea pig. One or two on each team will do. Ask them to join the board, and have them test changes before they go live.

“If you’re changing things on a rep, give them air cover. Say, ‘We’re going to run an experiment on a new commission system for you. But I’m going to guarantee you a 100% payout. That’s your floor.’ Of course, that doesn’t really mean as much to top reps who expect to blow their number out. But it’ll help convince most.” – Suresh Khanna,Co-Founder of Pieces

Simplify the CRM interface beyond the limits of breakability

Gated CEO Andy Mowat recommends simplifying sales workflows in Salesforce into buttons and pop-out forms. The reason being: If sales reps have to tap a combination of buttons to log a deal, and those buttons change, every rep will have to relearn how to log deals. But if you create one button that says “log the deal,” and it simply opens a form, you can change that form all you like. But reps will still know where to log the deal.

“You’re trying to do the least work possible. The simplest version of the system is the one that is as usable as possible for the team. Make it as idiot-proof as possible. Build buttons in Salesforce to abstract complexity into one click, and you can always change what happens after (using a tool like Form Assembly). For example, consider creating a button for:

  • New customer kick-off 
  • Legal and security review
  • Account data feedback
  • SDR meeting notes and call updates

It’s also a convenient way to allow contractors to selectively input research or update non-critical fields, generate UTMs, or kick-off approval requests in Slack.” – Andy Mowat, CEO and Co-Founder of Gated

“A common error I see: Not treating Salesforce as the sales team’s homepage. Even though they use ZoomInfo, have them navigate to it from Salesforce. One place to go.” – Sudhakar Jukanti

Further reading: Gated CEO Andy Mowat on CRM automation.

To pivot, you need resources

Companies invariably under-hire for support and operational roles. The challenge of course is that by the time you need these people (like you), it’s already too late. Now they’ll need to be hired and onboarded, and the organization has a bunch of issues that new person must work through before they can become productive.

There’s no surefire way to argue for these resources, but be sure leadership is aware of all the issues and future dependencies piling up, and make a case for hiring more people for your team sooner. If you have a recurring meeting with leadership, make this a point in every meeting, and tie it back to their goals. If they tell you they want to increase headcount, explain how those people won’t become productive unless supported.

“People under-hire their ops team. Especially growing ones. I always advise people to over-hire and hire senior. It’s better to have somebody who’s seen it before and can recognize patterns than someone who’s figuring it all out for the first time.” – Andy Mowat, CEO and Co-Founder of Gated

“If you’re overloaded with requests, give people options. Be very clear by saying, ‘You’ve asked me to do X, Y, and Z, but I can only do one of the three. Here’s how I’ve prioritized it. Does this match with what you’re doing? Would you like me to switch?” – Andy Mowat, CEO and Co-Founder of Gated

Featured experts

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 3 in Spekit’s course, Helping Sales Scale.


Want to get access to all the lessons?

Sign up now and you’ll get access to all the lessons and templates you’ll need to help sales scale.