A Founder’s Guide to Leading the Sales Team

We just launched a 27-page eBook, Building the Startup Sales Team.

The eBook was written for founders and other early startup employees who find themselves at the helm of the sales team without any prior experience. It’s the handbook I wished I had, just to point me in the right direction and get me focused.

I thought for those of you who want the short version (because, 27 pages!?), I would give you a quick summary here.

When we first launched our SaaS, I found myself accidentally at the helm of our sales function, responsible for building and growing our sales team.

Up until then, I had been making most of our early sales, with the help of a few sales-minded employees. Suddenly what had been somewhat ad-hoc (“Are there companies who want to buy this product?”) became mission critical (“Yes, there are buyers, now let’s scale it!”).

I was excited, I was nervous, and more than anything, I was ready to dig in.

Dig into what, I wasn’t sure. I didn’t even know what I didn’t know. I wished there had been a founder’s guide to running a sales team, but there wasn’t. So, here’s a quick recap of what I learned along the way:

• Recruiting—Start with hiring the right people.
• Quota & compensation—Create a compensation strategy that motivates and retains your team.
• Management—Manage, coach, support and develop the team to be high performing.
• Culture—Create the right environment for recruiting, retention and results.
• A sales process and methodology—Define and document how you sell.
• Tools—Implement the technology & foundation from which to sell.
• Hire your replacement—Know when the time is right for more sales expertise.

Everything you focus on as a sales leaders should be in one of these areas. Anything else is a distraction.

Recruiting

A successful sales team start with hiring the right people.

To land the right people, you need to be thoughtful and considered when it comes to hiring. You can’t wing it. Know who you are looking for and only hire those people. Salespeople come in all different varieties. You need to know who is likely to be successful.

Look for people who have sold something similar to your product/service. You can base that on price point, average sales cycle, buyer profiles, solution/industry, or a combination of both. If you hire someone without applicable experience (it will be tempting when you come across someone you like), it’s a risk, especially in the beginning before you can nail down the exact characteristics you need. Document the characteristics of your ideal salesperson, and be rigorous in hiring those people.

I’ve run a wild, wild west recruiting effort, and it’s messy and fraught with missteps. Even in the early stages, you want a repeatable process you can build on.

Quota & compensation

Create a compensation strategy that motivates and retains your team.

You won’t be able to hire anyone if you don’t know how to compensate them and give them a quota. If you are new to sales leadership, designing your compensation plan may feel like one of the most complicated things you have to do. You’ll need to decide on the total target comp, or on-target earnings (OTE). You will also need to determine quota, which can feel like throwing things against the wall to see what sticks. Don’t fall prey to over-estimating what a new team can do. Assess what you have been able to produce thus far from a sales perspective, and base quota on that. If you are really unsure, set a quarterly or bi-annual quota and re-evaluate after a few months.

Be strategic when considering your comp plan because you get what you incentivize.

Management

Manage, coach, support and develop the team to be high performing.

In the beginning, your sales team may just be you and a handful of account executives (AEs), but to scale you will need other players. Most modern sales organizations use sales development reps (SDRs) to book qualified appointments for the AEs. It’s efficient and effective and predictable. Most teams also have a sales operations function to support the department with the tools and processes needed to sell. Think of sales operations as the person(s) who clear the path of obstacles so the team can focus on selling. They find and implement sales enablement tools, create and advocate for content, and document and manage processes that help organizations scale.

A big part of management (and culture too) will be the measurement you put in place as well.

Culture

Create the right environment for recruiting, retention and results.

Your larger company culture matters for sure, but more than any other function, sales teams have their own micro-culture. Consider, and outline, the culture you want to create for your team and then use that culture as a tool. Recruit for culture fits, coach based on your culture and values, align your departmental plans with the culture.

Again, it bears repeating, because culture can be easily dismissed as the ‘soft stuff’ that doesn’t matter. It matters. Culture will help you recruit the best candidates, retain the best sales reps and achieve the best results.

A sales process and methodology

Define how you sell.

Processes help ensure you are measurable and benchmarked as you scale, and that everyone is living by the same guidelines and selling the same way. For example, it will be hard to ferret out why you lose so many new opportunities if everyone isn’t using the same definition of an opportunity. It will be hard to understand why the evaluation stage of the pipeline is stuck if everyone isn’t using the same criteria for deals in that stage. Your sales processes need to be documented and everyone needs to follow them.

A sales process is the steps and stages you take from lead to new customer. A sales methodology defines how those stages are executed. Think about the process as the steps and the methodology as the skills and approach for each step. You’ll need to define these things for your team, train them and reinforce them on an ongoing basis. Tools and a sales playbook can help.

Tools

Build the foundation with technology and playbooks.

Tools, like technology and playbooks, help make selling easier and help your team do it more predictably. You may start selling with a list of target accounts scribbled on a legal pad, but before you can blink you’re going to need a CRM to manage your leads and deals. And then you will need a tech stack that includes sales productivity, enablement, gamification, specialized analytics and more. A modern sales team runs on modern sales tools.

How those tools are used, and the processes around them should be documented in the sales playbook. A sales playbook is a collection of everything a sales team needs to sell and can be an indicator of a leadership style that extends beyond the playbook itself. It speaks to how well a team is run and managed. It demonstrates alignment, repeatable processes, accountability, expectation management. It guides the culture and coaching and ongoing investments into skill development of the team.  Sales playbooks help create a high performing team with repeatable processes and more predictable results.

Hire your replacement

Know when the time is right for more sales expertise.

How long founders can directly lead the sales team depends so much on the company, market and person’s aptitude.

If a founder is singularly focused on sales, and the team is crushing it, then it may be a permanent home. However, when a founder has many cross-functional responsibilities, as most do, or has hit the ceiling of what they can do from a skill and strength perspective, then a layer of sales leadership is going to be crucial. Without effective sales leadership, results will suffer.

If a founder can focus on sales and get the results, I am all for it. But I also respect when people know their limits. When I was leading my sales team, I was in my lane and loved what I was doing. But I also wore a lot of other hats in the organization including customer success and support, and some marketing responsibilities as well. Plus I was running the company with my cofounders. My time was fractured, to say the least. It worked for awhile, and we were growing fantastically. But I could see down the road and that I was nearing my limits of what I could juggle on my plate.

I had set the culture, the KPIs, the comp plans, the skill development, the tech stack…but managing it day-to-day was becoming daunting. The team needed more, so I ‘hired’ (promoted from within) a fantastic director of sales to be my partner. He was the yin to my yang and our skills complemented each other well. I piloted and he co-piloted. Until one day I looked up and realized he was in the pilot’s seat and I was in the co-pilot’s seat. The transition of power was seamless and effortless and without distraction or interruption for the team (which is essential). Bottom line: know your limits, and your strengths, and play to them.

You’ve got this!

Many talented, successful sales leaders started in a startup with no first-hand experience. Trust that if you stay focused on your team, your process and your results that you will be successful. Lay the foundation for a positive culture, accountability, and transparency. Build your repeatable processes and use technology as a tool to help you thrive. Adapt as you scale and learn. But most of all, stay focused on the essentials and stay available for your team. Good luck! And grab that eBook, Building the Startup Sales Team, if you want to dive into these areas more. 

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