Making the transition from founder-selling to having an entire sales team


Dive into the founder's playbook for transitioning to a sales team with insight from the CEO of Tigera. Key moves include strategic hiring, tailored training and ongoing involvement for sustained success.
The transition from founder-led sales to a dedicated sales team is a defining phase in a company's growth trajectory. 

This guide outlines the journey from making those initial hires to bringing on a sales leader, and finally, to the ongoing process of training and oversight. 

Let's explore the milestones and methodologies that can prepare your sales team for success and ensure your vision as the founder continues to drive sales long after you pass the baton.

When should you start hiring salespeople?

Contrary to what some founders might recommend, I believe you should hire sales representatives before considering a sales leader. This is vital during the phase where you're still fine-tuning your approach with early customers. By bringing on sales reps first, you get hands-on insight into the strategies and tactics that resonate with your market.

It typically takes about 3 to 6 months for a new sales rep to fully ramp up, so starting with two reps is a prudent approach. This smaller initial investment reduces risk and allows for more controlled growth. With just a couple of salespeople on your team, you can manage them directly and stay closely involved in the sales process.

Hiring two reps offers an additional advantage: It introduces variability. With two reps, you can conduct informal A/B testing in your sales approach. Each salesperson might have different styles or techniques, and comparing their results can provide valuable insights into what works best for your business. This data-driven approach can help you refine your sales strategy and build a strong foundation for when you're ready to scale up your team. Also, hiring two sales reps reduced the risk that comes from one of them being ineffective and you can rule out false negatives.

The right time to bring in a sales leader

Hiring a sales leader is a significant investment, and it’s a tough decision to undo — so don’t rush it.

You should consider introducing a sales leader only after successfully closing at least the first 10 deals (preferably yourself!). By then, you'll have a clearer understanding of several crucial aspects:
  • You'll have concrete answers to fundamental sales questions.
  • You'll know your average selling price (ASP) and the length of your sales cycle. 
  • You’ll understand the decision-makers in your customer hierarchy.
With this information, you can determine the type of sales leader you need — whether for field sales or inside sales, strategic or tactical.

A sales leader will be adept at scaling processes, but may not have the flexibility to rapidly iterate and modify the sales playbook. If you haven't established a repeatable sales process by the time you hire a sales leader, changing the playbook could be costly.

If brought on too early, without a solidified sales formula, a sales leader can lead to chaos and inefficiency. Hire a sales leader to scale a formula that works — not to create one from scratch. Hiring prematurely can set your business back by a year or more as you recover from a misstep.

Navigating the handoff from founder to sales team

Step 1: Do your prep work

Before a sales team can take the reins, it’s essential to have a clear and tested message. Debugging your sales messaging while still in the early stages allows for refinement before it's taught to a larger team. 

Step 2: Establish your processes

As a founder, you may have relied on instinct to guide you through sales interactions — but as you prepare for the handoff, it’s crucial to establish and document formal processes. This includes defining the sales funnel stages, criteria for transitioning between stages, forecasting methods and the steps for demonstrating POC.

Documentation is especially critical for aspects that may seem intuitive to you but may not be obvious to others. Every successful interaction, question and response should be recorded.

Set clear exit criteria for each sales stage so each rep understands exactly what must be accomplished before moving a prospect to the next phase. This structure prevents ambiguity and ensures that the sales team does not advance a deal prematurely, which is crucial for maintaining a robust and predictable sales pipeline.

Step 3: Set up a robust, scalable training program

The transition from founder sales to a team approach also means you’ll need a comprehensive approach to training. 
  • Sales enablement.
Sales enablement at this stage involves leading your reps through the nuances of your product and the market. Start with the basics — bring the reps into a collaborative environment and engage in interactive sessions like whiteboarding, which can help cement their understanding.

Your reps don't need to know every technical detail of your product, but give them a conceptual grasp of the basics. Don’t overwhelm them, but they should be equipped with enough knowledge to communicate the value proposition confidently and earn the trust of prospects. Understanding the technology also enables them to effectively address questions and concerns.
  • Teach them sales and a conceptual understanding of the tech.
Training should also cover how to identify and pursue promising leads. Teach your sales reps to recognize the signals and indicators of a good prospect. It’s crucial to differentiate between a prospect worth investing time in and one that is less likely to convert.
  • Codify everything.
Again, during the training process, document everything — from prospecting techniques to sales strategies. This documentation will serve as your training manual so that all sales reps, regardless of previous experience, have a consistent approach and a clear understanding of expectations and methodologies.

Pro tips for making a smooth transition

When transitioning from founder selling to a full sales team, keep these recommendations in mind:
  • Bring in a sales pro: As a founder, your expertise is your business. You’re not necessarily fluent in the language of sales. It's beneficial to get coaching or advising from an experienced sales professional to bridge that gap. They can help you understand and communicate in ways that resonate with sales teams.
  • Understand it's not a binary switch: Moving from founder sales to a team is a gradual process, not an instant change. Take the time to ensure that the transition is smooth and that all sales processes are clearly understood and established.
  • Stay involved: Even after the sales team is in place, it's crucial to keep checking in. Attend forecast calls and use tools like Gong to listen in on sales conversations. This allows you to identify and address execution gaps quickly.
  • Stay in touch: If you notice discrepancies or areas for improvement, communicate with the sales leader to address them promptly.
Remember, the goal is to establish a sales operation that is self-sustaining and remains true to the company's vision and standards. Regular oversight and strategic input can help maintain balance as the company grows.

Building a sales team: A founder's journey from first hire to full force

The progression from founder-led sales to a robust sales team is more marathon than sprint — and the transition requires strategic hires, systematic training and vigilant oversight. As I've experienced with Tigera, these steps are crucial:
  • Start by hiring a few sales reps to fine-tune your approach and understand your market.
  • Delay recruiting a sales leader until your sales process is well-defined and proven.
  • Develop comprehensive training and documentation to ensure consistency and clarity.
  • Stay hands-on with the process, using advisors as needed and continually checking in to maintain a healthy sales execution.
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