7 Tactics to Make Founder-led Sales your Unfair Advantage

The Dock Team
March 21, 2024
July 3, 2024

As an early-stage startup founder, you are the best person in your company to close deals. 

If you’re an introverted developer-turned SaaS founder, you are probably skeptical right now. But you don’t need to be an exceptional salesperson or closer to do founder-led sales.

As the founder, you have many unfair advantages that can help you excel in the B2B sales process that even a seasoned sales leader doesn’t have at their disposal. 

For starters, you understand the product, the market, and the company vision better than anyone else on your team (and you always will). 

Not to mention, it feels special for the buyer when they get to talk directly to the founder. You can use this to build relationships and get valuable feedback for your customer success team.

In this post, we’ll share why embracing founder-led sales can give you a competitive edge, how to do it well, and when to step away and build out a sales team.

Why should founders do sales?

Founders have a unique perspective on the business’s products that can drive interest, build trust, and provide valuable insights that show how the products can solve clients’ problems. 

When founders engage directly with potential customers, it helps establish a personal connection with prospects that a sales rep can’t replicate. 

Prospects get to experience firsthand how involved and knowledgeable the founder is and see their genuine enthusiasm for their business. This interaction quickly builds trust and confidence in the product. 

The founder’s in-depth understanding of their products and the market they are in allows them to address customers’ pain points thoroughly. 

For example, in the earliest days of Dock, Alex Kracov, our founder, would do things that didn’t scale, like offering to build a custom Dock space for prospects after a demo call. This greatly reduced the friction for our earlier users to get started and see immediate value.

Founders can also use their personal insights, authenticity, industry expertise, and adaptability to help strategically guide sales that can accelerate customer acquisition and position the company for sustained growth.  

Founder-led sales tactics

Here are some founder-led sales tactics that can help you turn more leads into closed-won deals.  

1. Use the sales process to get valuable customer feedback (and vice versa)

Leads and clients are often willing to provide honest product feedback throughout the sales process—especially when they’re talking to the founder.

These early sales conversations are critical for helping you identify areas of product refinement, provide insights on how your product addresses their pain points, and improve customer satisfaction and retention. 

Not to mention, as the founder doing all of these demo calls, you’ll start to see patterns emerge. You can then relay this information to your team. You can use this information to help perfect offers, ensure you’re targeting the right audience, assist with product or service refinement, and product decisions.

It can also be a sneaky sales tactic by asking ideal-fit prospects for product feedback. If they have a good experience, they might turn into a customer.

2. Drive more upsells and cross-sells

Founders can strategically identify upselling and cross-selling opportunities through the product feedback process, too. 

The information gathered can provide a deeper understanding of customers’ needs and preferences, allowing for personalized recommendations on additional services or products that can further support customers.

For example, let’s say you build project management software for agencies with a per-seat pricing model. You originally sold the agency owner on an initial pilot for them and their two account managers. The pilot is going well, which makes it natural to upsell them on bringing their entire team over to your platform.

Note: Because you are the founder, you can often get away with a more personalized, casual approach to all of this by sending texts, emails, and hopping on quick calls.  

3. Niche down

When you are raising money, you need to paint a big picture to VCs. However, this is the exact opposite approach you need to take with your early sales process.

Our founder Alex adds

“One of the mistakes I made early on at Dock was trying to build for too many use cases. I wanted to create a horizontal product for any type of business-to-business interaction, from sales to recruiting to finance.

But this proved to be an enormous challenge on many levels.

1) Customer feedback was all over the place - when we went to talk to customers we heard such a drastic range of things to build. For example, recruiters wanted Dock to integrate with ATS systems, while sales teams wanted us to integrate with CRM systems. We couldn’t build both with our limited resources.

2) Product experience was too open-ended - since we wanted to build a horizontal product, we tried to build a super flexible product experience. But this decision led to an activation issue for our customers. The product wasn't tailored enough to actually solve for any one persona’s challenge.

3) Hard to define our positioning - since we needed to speak to many different people, we had to create generic messaging that spoke to no one.

4) Difficult to gain GTM momentum - when running ads or sending emails or reaching out to folks on LinkedIn, we tried to go after too many personas. We weren’t able to create content that resonated, since we had too many goals. We spread ourselves thin across personas which limited the amount of organic word of mouth growth.” 

Niching down allows you to focus on a specific customer audience, so you can: 

  • Stand out from competitors
  • Provide a specialized product tailored to address that audience’s specific needs
  • Show a deep understanding of the industry and its unique needs
  • Develop targeted marketing messages

For example, as DataRobot’s Ben Solari shared on our podcast, they initially had a horizontal product. But instead of trying to cast too wide a net, they focused on a handful of really specific use cases for specific segments to get early traction.  

4. Create a repeatable sales process that scales 

Founding sales tactics are powerful but can also be time-consuming. 

One way to save time is to create sales templates to help streamline calls, emails, and interactions. This will also be a valuable asset once you are ready to build your sales team.

The templates ensure you provide and gather the core information you need but also allow room for you to tailor interactions. Personalizing interactions will help you gain valuable insights and adapt messages to address customers’ unique needs and concerns.

In fact, these are the exact email templates that our founder and CEO, Alex, created:  

  • Inbound Demo Request - email I sent when someone requested a demo on the website. The goal of this email was to schedule a demo call.
  • Demo Follow up V1- email for folks who wanted to move forward with Dock. The email includes action items about the pilot program, setting up a template, and next steps for onboarding.
  • Demo Follow up V2 - email for folks who were still deciding whether they wanted to move forward with Dock. This email included action items, but had softer language around the timeline (“whenever you’re ready” language). 
  • Demo Follow up V3 - email for folks who were not really interested. The email thanked them for their time and said we’ll stay in touch as the product evolves.

When you create these template emails in conjunction with your digital sales room in Dock, it is an easy way to collaborate and share information throughout the sales cycle

Plus, you can quickly duplicate it and then add a few personal details for the next prospect. 

5. Identify sales objections and turn them into opportunities

Jenny Beres, co-founder of Pink Shark PR, recommends turning regularly occurring sales objections into opportunities

Look for objections that you or others hear frequently during sales calls or other parts of the sales process. Then, look for ways to overcome or address the objection. This step may require examining your sales and marketing playbook, including:

For example, we often heard skepticism as to whether customers would actually engage with a Dock workspace during the sales process. Sales reps were worried their customers might not engage with Dock. So, we made this guide to introducing customers to Dock, including quotes from real customers on how they get customers to engage.

Then, you can use your sales conversations and demos to explore the objections and look for solutions.

6. Build in public on social media

Sharing your story and what you are building on social media, like LinkedIn, can help you get more people invested in what you are building.

  • Understand current issues and problems your customers face
  • Showcase your expertise
  • Build meaningful connections through helpful and educational content
  • Identify potential partnerships with businesses or people offering adjacent services or products
  • Engage with leads through direct messages

For instance, when we brought on our first sales and customer success key hires, Alex documented his approach in a series of LinkedIn posts, including this one. 

Any founder can replicate this by simply making a point to share one thing they did this week on LinkedIn. If you do this consistently, this will get more people invested in your story, and as a result, generate more inbound leads and more closed-won deals. 

7. Keep the momentum going with a strong customer onboarding process

Sales doesn’t end with a signed contract. You still need to successfully onboard them on your product. In the early days, you, as the founder, should own both the sale and the early onboarding process. That’s because a great onboarding experience is the single, biggest predictor of renewal.  

Bonus, if you’ve already created a digital sales room in Dock, you can also use this as an onboarding workspace. So, you can map out and include all of the steps to ensure a smooth transition, like your timelines, onboarding resources, surveys, etc.   

How to transition out of founder-led sales

While founder-led sales is a powerful strategy, you’ll eventually need to remove yourself from the day-to-day sales process to scale your business. Because at some point, you won’t have the time to be involved in every direct sales call and you’ll be the bottleneck to growth.

However, the transition from founder-led sales to building a sales team is a difficult transition. According to Jason Lemkin, most startups’ first Head of Sales hire doesn’t work out. 

Even if your first hire is exceptional, you’ll likely still see a drop in your win rate and a longer sales cycle. At least initially—because you have to go slow and train them on your sales process. You can minimize this by creating a clear sales and marketing plan that allows you to slowly and strategically transition out of founder-led sales. 

Here are some tactics that can help you successfully transition away from founder-led sales.

1. Don’t delegate sales too early

If you are not a natural salesperson, there will be a temptation to delegate sales as soon as you start to see any repeatable patterns. But, this is a classic trap. 

In fact, Peter Kazanjy, Co-Founder of Atrium and author of Founder Sales, doesn’t recommend transitioning until you have done at least 50 sales demos and have a repeatable win rate of 20% or higher. Then it might be time to hire your first sales rep: 

2. Be thoughtful about your first sales hire 

The first step is to decide whether to hire a Head of Sales or account executives, initially. Both can work, but you need to be clear on what the business needs.

💡 Pro Tip: If you go the AE route, it is a best practice to hire two initially. That’s because it provides a natural opportunity for benchmarking, makes training a bit easier, and also safeguards against some of the most common downside risks. 

Trying to wing your first sales hire is a recipe for problems. Having a detailed sales hiring process ensures that you gather all the information you need to make the best decisions for your company:

  • Create a hiring scorecard that identifies key attributes and skills needed to successfully sell your product so you have a clear understanding of the qualities you need
  • Not rushing the hiring process so you get the best-fit candidates

One thing to pay attention to is that salespeople are naturally good at interviewing. It’s why they’re good at sales.

This means you need to dive deeper in the questions you ask them and finetune your bs radar.  For instance, Tomasz Tunguz recommends asking these three questions:

  • “Knowing what you do about our business, what kind of sales methodology would you run? And how does that compare to your previous role? What are the differences between your previous company and this one?
  • What kind of salespeople would you hire, and how do they differ from the people you have hired in the past?
  • How would you structure the compensation plan to meet the needs of our business?”

3. Hire a systems builder, not a closer 

Many founders think they just need to hire a rockstar account executive, who is really good at closing deals. While that might help in the short term, it can actually backfire as you build your sales team.  

For instance, Todd Busler, former first sales hire at Heap, says the first sales hire sets the foundation for your company's sales machine.

"I was the first rep at Heap,” says Todd. “I'm not the best rep. If you drop me at a mature company right now I'm not going to outperform everyone. I think what you are looking for is someone who is really comfortable with ambiguity, comfortable with trying a bunch of different ideas where you know a high percentage of them aren't going to work, and someone who is really good at documentation.” 

Your first sales hire is building the machine. Because of that, you need a sales manager who can sell but is even better at building sales operations from the ground up. This means they need to be able to communicate effectively with you (the founder), your product team, and other company leaders. 

4. Give your new hire the chance to demonstrate their sales chops 

Chances are, if you made the right hire, your new salesperson is going to be eager to show you what they can do. Once they are trained up, you need to be willing to delegate the reigns since this builds trust.

For instance, Robby Allen helped his company, AgentSync, move upmarket by helping the founder through the handoff process as their VP of Sales.

“I had to show them that I could sell day one and putting points on the board was my singular priority for the first month,” said Robby.  

But, it wasn’t enough to just sell, he needed to show how he could do it in a systemic and scalable way. Over time, this earned his founder’s trust.

5. It’s okay to micromanage your first sales hire 

This next point might seem counterintuitive. However, as Peter Kazanjy, Co-Founder of Atrium and author of Founder Sales, mentions, it is easy for founders to be too hands-off once they trust their new hire.

Peter recommends treating your first few sales hires like “line cooks.” 

You wouldn’t promote a line cook to executive chef of a Michelin Star Restaurant without an extensive training program. The same applies for your first sales hires.  

All of the processes you’ve been creating and iterating on up until this point are now extremely useful when it comes to training up your new sales hire. 

While this process might look different for every startup, some key components Peter recommends are: 

  • A documented demo flow written out 
  • A sales deck that you are actively using 
  • Recorded sales calls in Gong 
  • Then, have your new sales hire initially shadow you on calls, then you shadow them on calls, and finally a definitive process for certifying them. 

6. Stay involved with sales, but don’t lead each sale                                                                                                                                                                 

As your business grows and your new hire becomes more independent, you won’t have the same amount of time to spend on direct sales. However, this doesn’t mean you should leave all aspects of sales to your newly hired sales team. That’s a recipe for disaster. 

On LinkedIn, our founder Alex said: 

“The key to a successful transition is for the founder to still be deeply involved with sales, but not lead each sale.

To be honest, I’m still figuring out this balance, but here’s what this means for me:

I’m no longer joining calls as the “sales rep.” I’m joining sales calls as the sales engineer & product manager.

As the person leading our product development, I’m able to answer super technical questions about our product and discuss how we’ll fit into a customer’s tech stack.

I get to leave all the qualifying, timeline setting, price negotiations, etc. to the pros. Thanks Joey & 🤙 Andy.” 

While he is not driving each sale, he is still deeply involved when it comes to being a master connector—both for building relationships with decision-makers as well as with product expertise.  

7. Incorporate founder-led marketing tactics

Another way to maintain an active role is by using founder-led marketing strategies that support your sales team without needing to be involved in every call. 

Founder-led marketing focuses on creating marketing assets that provide essential information about your product and company, including addressing pain points and overcoming common objections. Then, your sales team can also use the information throughout the sales process.

For instance, one way to do this is by investing in your personal brand on social media. An example of a CEO who does a great job of this is Peter Caputa of Databox. Databox has a product-led growth strategy and Pete empowers his sales and marketing team with a ton of content they can use in their campaigns. 

Subscribe to Grow & Tell for more insights

Founder-led sales can help build authentic relationships, shorten sales cycles, and build trust because prospects love to talk to founders. 

However, you’ll likely need to develop a strategic plan to help you transition from founder-led sales to a sales team as your company scales. But this transition doesn’t have to compromise your brand. You can slowly transition out of direct sales but still stay involved and support your sales team. 

So, your company’s voice and expertise, authority, and in-depth knowledge remain key components of your sales process. 

For more founder-led sales insights, subscribe to our podcast, Grow & Tell — where we share the builder stories behind the most successful B2B companies.

The Dock Team