How to scale a sales team: what the different stages of growth require from sales leadership

Collin Stewart, CEO

9 September 2019

Hyper growth: that always desirable, but often elusive, stage of growth. 

In one way or another, we’re all trying to get there. But this isn’t an overnight thing – arriving at hyper growth is a journey, one often fraught with missteps, experimentation, and flat-out mistakes. 

But, despite the fact that every company journey is unique, and everyone will, at some point, face difficulties in their pursuit of unicorn status, there are specific stages of growth that require a specific set of skills both from sales leaders and individual contributors.

And if you know about those general requirements, maybe (just maybe) you can navigate these challenging waters with a little more ease.

“I like to draw parallels to sports. I played a lot of sports growing up – particularly basketball. So, at the three stages of sales growth, I look at them through the lens of the plays you’ll be running at each,” says Robby Allen, founder of Buena Vista Ventures, on a recent edition of The Predictable Revenue Podcast.

So what are Allen’s three stages of sales growth? 

Product market fit – all you’re trying to do here is find an opening in the market (a mismatch) and leverage that opening to survive. Survival is key!

Repeatability and scale – at this point, you’re running a defined play, and you have a high degree of certainty that things are going to work out. But, despite the inherent “busyness” that comes at this stage, there’s only about 1 or 2 plays you’re running here. Don’t make things too complicated.

Hyper growth – okay now you have a full playbook. You can run situational plays, you’re comfortable in loads of different scenarios…and you’re crushing it.

Product market fit

Product market fit represents the early days of sales growth – you’ve seen some traction, deals are getting closed, but your path to the promised land isn’t yet clear.

The keys, according to Allen, at this stage are simple: survival at all costs, don’t get too fancy, hone in on what is working (find those mismatches), and make sure you bring on “utility players.”

“If you are a leader or a first sales rep, the goal should be to survive. That sounds dire, but in our world, and the time we have to drive results, you have to survive here. So, where can you exploit your advantages? Is it your product? Is it the size of your market? Your investor network? What can lean on early on to drive wins?” asks Allen.

“You don’t yet have an architected play that you can run over and over again. But, with a small tight-knit team, you can really exploit what you know works.”

On top of the closeness of your reps, it’s imperative you hire team members that can navigate the varying pressures of a startup (the aforementioned utility players), adds Allen.

At this stage, you may have to demo an enterprise client one minute. Then, you may be called upon to prospect leads another minute. Or, you may even have to juggle some customer success responsibilities. Whatever the task at hand, your team needs to have that “get it done” mindset and tackle any of the challenges thrown their way.

At this stage, you can have anywhere from 2 to 10 reps (try and hire 2 at a time to promote some competition and give your new reps someone to lean on). All of these reps will be rolling up to aHead of Sales, or a manager for the more junior members of the team.

“You want a team that can adapt and adjust. Don’t forget: mistakes and successes can be fickle. You can overestimate how strong a mismatch was and you may need to adjust ASAP,” says Allen.

“It takes a certain kind of salesperson to deal with that, and not complain about the changes they need to account for.”

The same is true for sales leaders. For example, you will have to perform all of the expected coaching duties during the day, as well as chart a path forward for revenue growth. But, you may also have to juggle sales operations and enablement…off the side of your desk. Someone has to make sure that your CRM is chugging along.

“As a sales leader, sales operations is on your mind a lot during that time. So, of course, you want to hire for that. But, what you really need is to get to repeatability. Then, sales ops becomes really important,” says Allen.

“So, you are kind of running the recruiting process in tandem. But, in those early days, sales ops is really a job to be handled by the Head of Sales or Sales Manager.”

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Repeatability and scale 

At this stage, you are ruthlessly measuring everything you are doing to determine whether or not your plays are worthy of investment. Sure, you’ve developed a couple, but iterating and evolving is crucial, so make sure you are always looking for more (as you crush what has been working).

For example, Zenefits, where Allen led sales, was an inbound shop at first. But, they needed more, so they tested outbound. The idea was: if they could reasonably get their reps to 24 opps per month, and close X number of those deals from those opps, outbound would be profitable and they could expand the experiment.

“At every level, develop the play, run it, measure it, and be able to predict your win rates. If you can do that, you have something that can work. That will get you to repeatability and scale,” says Allen.

“One of the hardest things to do is get to repeatability. It is extremely hard, in fact. But you have to take advantage of a mismatch, run your plays consistently and demonstrate that predictability. This gives leadership a story to tell investors.”

And when should you expect to see this level of sales maturity? How big is your company? According to Allen, this is likely to happen closer to a Series B or Series C round of investment.

As for your sales team, you can expect to have between 10 and 25 reps, all of whom will be segmented in a clear sales structure with prospectors prospecting, closers closing, and account managers managing accounts (accounts are segmented as well – by size, geo, or other criteria).

That level of control should definitely be in place by this point.

Finally, that long-awaited sales ops and / or sales enablement hire (hires) has been brought on. Remember: measurement is huge here, and sales ops are critical for that. Sales enablement, on the other hand, can help ramp up new reps and develop the skills of your existing team.
(Editor’s note: we had Kelly Del Curto on the pod a few week’s back to discuss the power of coaching and long-term goal setting with your sales team. You can read about our chat here, or listen to the whole in-depth interview here)

Getting to hyper-growth

You’ve made it! Congratulations! You must be crushing it.

Actually, if you’ve made it this far, you are crushing it – there’s no other route to hyper-growth. 

But, be warned, there’s more to hyper-growth than just destroying quota: your sales leadership team is also able to predict your sales number month over month, you have multiple plays that you can run with ease, and you are keenly aware of your competition (by this point there are like 2 or 3 companies vying for supremacy in any given market).

“I have been fortunate to jump to this part of the journey twice. If you get there…good job. You should feel really good about that,” says Allen. 

“And the goal becomes very simple: win your market. So, it is all about execution.”

A fundamental piece of execution at this stage – one that isn’t readily associated with sales all the time – is customer success. A huge part of navigating hyper-growth is keeping your customers happy. You can’t grow the way you did at previous stages: either you or your competitors, have signed a sizable chunk of the market. Therefore, ensuring your customers don’t walk out the door is critical. For example, you can’t have 5% monthly churn. You will be exposed if that is what is happening. Churn is a top risk at this stage.

Finally, your investment in sales operations at this stage is likely increasing. 

With multiple cities and multiple geos for targeting, the value of sales ops and enablement has scaled concurrently with the business. When the team matures to this point, sales ops can even take on more leadership responsibilities. For instance, leadership meetings can even be led by sales ops.

When you get to something like 200 sales reps, as Allen experienced, it becomes harder and harder to spot personnel problems. Sales ops, however, make sure that any kind of quantitative gaps in performance can be spotted very quickly. At Flexport, for example, Allen says, one of the issues they had early on was that the team wasn’t closing some of their targets as easily as they had anticipated. 

So, they dug deep and we were able to drill into the average title of the person they had closed historically. That deep dive allowed them to adjust accordingly and sharpen their outreach. Allen, with all of his responsibilities, could not have generated such a report. 

But ops could – and it was a HUGE lift.

“Remember: your goal is to win the market at this stage. And to do that you need to remain flexible. Maybe you over indexed on one particular play. Or, you didn’t keep iterating and innovating on your processes,” says Allen.

“If you are a leader that has made the jump to this point, you have to be relentless on getting people to own things, be dedicated to innovating, and leading your team into new places. Don’t forget that.”

For more on Allen’s thoughts on sales growth – including some tips on how to hire at different stages – check out the rest of his interview on The Predictable Revenue Podcast.