From scrappy sales reps to buttoned-up account management

The TLDR Snapshot

Sales teams and processes look very different as companies look to deliver sustainable growth at much larger numbers.

  • Early sales people are scrappy, creative individuals who find the revenue
  • Sales in the scale-up phase brings process and predictability
  • Mature sales organizations specialize, focus on account expansion

How Sales in Professional Services Grows Up

The saying “everyone is in sales” is never more true than during the early years of a start-up. But at some point sales must mature into a focused, scalable, sustainable function. Having spent more than two decades in enterprise sales – the last 10 leading professional services teams – I can tell you a LOT has changed in sales.

However, companies face some consistent challenges when growing sales from a team of one to hundreds or thousands globally. Some of these companies manage the shifting tides better than others, but knowing what to expect and focus on in these different phases can set you up for success.

The Startup Years: Contained Chaos

In the early years, every employee from top to bottom is in sales, tapping their networks to find the clients that will give the company a shot. This works because when a company’s brand is relatively unknown and customer references are limited, clients are really betting on a person they know and not the company.

At some point, you’ll hire your first sales people. The profile of a start-up sales person is very different than the profile of those you’ll want to hire later, but those who are successful in the early days tend to share some common traits:

  • They’re scrappy. If you grew up on Scooby Doo, you likely remember his nephew, Scrappy Doo. He had boundless energy and never let rejections deter him. These sales reps are living, breathing examples of Winston Churchill’s maxim that “success consists of going from failure to failure without loss of enthusiasm.”
  • They’re not process-people. They tend to have the mindset of “just get it done”. Oftentimes their deals are not fully baked, qualified or in the company’s sweet spot, but they find the revenue. They tend to have a high degree of creativity when it comes to shaping a deal because they know the results they deliver are the lifeblood of the company.
  • They’re comfortable in a start-up. This one seems like a no-brainer, but we’ve all seen the start-ups that think if they hire a successful rep from Large Technology Company X, they will immediately be successful. In fact, these reps tend to expect lots of sales support: instant access to collateral, carefully honed messaging, and lots of in-bound opportunities. None of which are typically present in an early stage start-up. Make certain your early sales hires have a history of surviving and thriving in the chaos of a start-up.

As the company grows, you’ll start to see signs that what got you here won’t get you to the next level. Process becomes much more important, and suddenly, adding more Scrappy Doos just adds to the chaos.

The Scale-Up Phase: Rocketship Growth

At some point the scrappy startup needs to grow up, and you’ll hit a point when you need a sales team that can deliver sustainable growth even at much larger numbers. Companies hit this point at different times, but the warning signs look something like this:

  • Deals that you would have jumped at a year ago don’t make nearly as much sense as they used to when any size deal or customer would do.
  • The lack of qualification gets to be a much bigger problem. The endless tailoring required to manage a deal that doesn’t fit your company’s sweet spot starts to burn out your operations people and delivery team.
  • It’s taking too long to find and onboard sales people who can serve your customers, and you have no visibility into how you’re going to make the number. It feels like a knife fight every time.

If it feels like you’ve run up against these challenges, now ask yourself these questions:

Do you know who your ideal customer is and how you address their needs? There’s a learning curve for every company. What’s great about Scrappy Doos is that their lack of discipline about fit means you’ll learn quickly which customers are a perfect fit where your teams routinely deliver amazing results, and the customers where everything is a struggle. This is the perfect time to assess your wins and losses to see if a pattern emerges. What does your ideal customer look like? What level and roles should you be targeting? Which solutions lead to bigger deal sizes?

Do you understand how customers effectively move through the funnel? For most startups, this answer is a resounding no because Scrappy Doos thrive by finding their own way. However, if you start to bring on more sales people faster and everyone has a different sales process, it will cause internal friction and waste time. If everyone talks about their offerings, solutions, clients and sales pursuits differently on forecast calls, that’s a clear signal that you need to align on a common sales vocabulary and methodology. Whether you prefer BANT or MEDDICC doesn’t matter as much, in my opinion, as having a process that is consistent and customized to your business. Consistency enables scale.

Do you know what sales activities really move the needle? This takes some real introspection about how stuff really gets done within your org, hopefully supplemented by some real data. Do you know what messaging and activities drive success and which are just wasted effort? Knowing this will help drive a more standardized and reliable sales motion. Document how different sellers approach sales pursuits. Spend time listening, and do “ride-alongs” so you can take notes and provide coaching. Do post-mortems around lost deals, internally or if you can with the actual customer. In my experience, many customers will take the time to provide frank feedback as long as you make it clear that you’re trying to learn, and not trying to push them into buying.

If you need help answering these questions, it’s a good time to start searching for a proven, experienced head of sales. Ideally you want to hire this leader before you start hiring a large number of reps. Otherwise, the new leader will likely spend their first few months having to undo many things that have been put in place.

The right leader should be able to:

  • Align the team around messaging and a differentiated value proposition
  • Partner closely with marketing, finance, delivery and product teams on go-to-market strategy
  • Define consistent and closed-loop sales processes
  • Develop sales rep hiring profiles and effective onboarding plans
  • Define compensation and incentive plans
  • Define and map territories and target markets
  • Refine the existing channel/alliances strategy
  • Develop a consistent forecasting approach
  • Build out a scalable RevOps platform

Look for a leader who can help drive consistency and predictability into the sales process, and has a process for turning those early-stage scrappy sales reps into team players.

The Mature Sales Org: From Projects to Programs

Once you’ve identified your ideal customer profile, built consistent sales processes, proven consistency in scaling sales, and built out a team that can drive growth objectives, it’s time to start thinking ahead to what customers look like and what they might need from a long-term partner.

  • How does the profile of salespeople evolve to grow accounts, not just land them?
  • What skills and internal processes are needed to manage a $5M account vs. a $1M account?
  • When will you outgrow your current org structure?
  • When do you need to go deeper into verticals?
  • What’s the next market or solution you should be looking to target or acquire your way into?
  • How do incentives need to shift as you move into new models or markets?

Though having a mature sales organization may seem like years down the road, the earlier you begin planning for it, the better off you will be. You’ll be able to do things like:

Accurately forecast and plan ahead for more predictable revenue: A consistent qualification and sales process will result in more dependable and accurate data, which will allow you to answer vital questions like: How much new pipeline needs to be generated each quarter for a rep to achieve their goals? What percent of deals that move to the propose stage actually close? What is our average deal cycle length?

Move to new markets more confidently: In Inside the Tornado, Geoffrey Moore refers to this as the bowling pin strategy. It allows you to build on previous successes to move faster and more easily to adjacent or complementary areas, tweaking processes and messaging rather than building from scratch every time.

Make sales people productive, faster: Mature sales organizations know the activities, milestones and measures required for a new salesperson to become successful, and can measure progress by more than just quota achievement. Having a roadmap for success means you can onboard more people, faster and know quickly when it’s not the right fit.

Grow accounts and increase Customer Lifetime Value: There comes a point when organizations tend to bifurcate into account executives that manage projects and client managers that manage broader programs. Both play a role in revenue growth, but having experienced salespeople with a background in delivery and program management becomes more important if you want to build larger, longer tenured clients,

Rome was not built in a day

Building a mature, high performing sales team that provides predictability and scale is no small undertaking. It’s easy to get overwhelmed by the task at hand so start building the foundation with small but important steps:

  • Ask your clients why they bought and what the experience was like.
  • Start doing post-mortems around lost deals. Try to talk to the prospect if possible.
  • Examine the historical data in your CRM to see if it’s good or bad data, looking for patterns and gaps in your data.
  • Begin documenting how your reps manage their opportunities.
  • Choose one sales activity you know from experience provides value to a sales process and start having your reps do it consistently.

These are just a few steps that can help start you on the journey, but continuing with these types of activities will help identify areas to improve and ultimately achieve your growth goals as the company scales.

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