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How To Do Founder Led Sales at Scale

Ben Borton, Feb 10, 2025

AI tools make sales an order of magnitude more efficient, just not in the way most people think.

The conventional view of AI’s impact on sales is that “the old tradeoffs between scalability and personalization is disappearing.”

But if everyone has cheap access to the tools of mass personalization, does that aspect of sales become less effective? I think the average quality of sales communication will increase and the volume of communication will go through the roof. 

I see the impact of AI in my LinkedIn inbox, which is littered with a flood of fairly good impersonations of personalization, 100% of which go unanswered because I have no relationship with the sender. The quality of copy writing has gone up, but so has the ratio of noise to signal.

The true sales efficiency gains from AI will come from amplifying the most human aspects of sales rather than replacing them.

An individual founder can use AI tools to supercharge the aspects of sales that AI is not good at: unique content and relationships. 

Founder-led sales, which has historically been thought of as “doing things that don’t scale”, may now scale much farther than previously believed.

What is AI Good At?

AI is exceptional at creating real time transcripts and summaries. Tools like granola.ai have reduced the administrative burden of the PodPlay sales process by at least 75%. Getting accurate notes of meetings and next steps into Hubspot and Slack happens with the press of a button. What used to take more than an hour per day now takes 15 minutes at most. 

AI is also great at certain types of content creation. AI uses math to determine the most likely answer to a question or prompt, so it tends to be good at producing content that looks like the average of all other similar output. Sales communication templates and follow up emails are made easy, consistent, and time efficient. Brainstorming ideas and producing an SEO optimized infographic is made trivial. 

But the best content is not average. It tends to break patterns or establish new ones. 

Outlier Content

The very best content succeeds because it fills a knowledge gap, provides new insights, or makes readers think about a topic in a new way. It may build off of old patterns or templates, but there is always something new and different about the most successful content. If we map content into a normal distribution, AI is great at the middle of the distribution, while the best individual content creators represent the right tail of the distribution. Content today lives in purely digital form. As a result, great content can scale infinitely and naturally tends towards a power law. A blog costs the same to produce whether it reaches 10 people or 10 million.

Relationships

Relationships matter, particularly when serving small businesses (SMB). I think it is unlikely that SMB entrepreneurs will buy essential vertical technology solutions from AI Agents any time soon. Owners of small businesses tend to buy from people before brands. As a result, a founder-led sales motion should produce higher win rates and shorter sales cycles in SMB verticals.

The conventional view is that a founder-led sales motion can work until $1 million in ARR (or some other heuristic indicative of product-market fit). At that point, a sales playbook is established and a sales organization is hired to scale the process. But does this view still hold?

At PodPlay, we believe the changing nature of technology simultaneously makes a founder-led sales motion more effective AND far more scalable. 

The PodPlay Flywheel

PodPlay’s Go-to-Market (GTM) motion couples content-based lead generation with founder-led sales. Digital content is highly scalable AND becomes a form of relationship building at scale. Our goal is to have the best product and the best content. If we can do that, we will have a highly efficient GTM motion that allows us to reinvest in R&D that in turn increases our product lead. 

Our GTM motion helps power the PodPlay Flywheel:

the-podplay-flywheel.png

The Four Pillars of the PodPlay Content Strategy

We serve two audiences: sports clubs and the end customers of those clubs. While the clubs are our clients, they succeed insofar as we create an amazing experience for their end customers. 

We have different types of content that speaks to our target audiences:

Short Form Video. These have viral potential, are highly engaging, and drive brand awareness. Short form video content includes replays and shorter segments clipped from long form video and / or podcast appearances. We publish content on Instagram, YouTube, and LinkedIn. Examples include:

Long Form Video. We launched The Joy of Pickleball series with Kaitlyn Kerr in Q3 2024. We send Kaitlyn out to a PodPlay club once a quarter to capture the fun, the people, and the stories of great venues. We see our mission as building tools that increase the amount of fun in the world. The Joy of Pickleball has been effective for broad brand awareness AND as video case studies that can be shared with prospects. We publish long form videos on YouTube and do posts on LinkedIn and Instagram to drive traffic to the long form. Examples include: 

Podcasts. We have yet to launch our own podcast, but we regularly appear on podcasts. Long form conversations captured in digital form allow potential customers to “get to know” the founder and the offering before meeting them. Shorter clips can be used to support other content and build relationships with audiences. If you think of your favorite podcast, you likely feel you “know” the host. This is a form of relationship building at scale. Examples include:

Long Form Blogs. We seek to publish usable insights based on real experience running 20+ of our own clubs. Each blog addresses a key pain point for clubs, provides a framework for thinking about the problem, relevant data, and the PodPlay solution. The common theme is how to drive club ROI through features that increase revenues and decrease costs. The blogs serve prospects actively researching and as demo follow ups. Our primary distribution channel for the blogs is LinkedIn and our website. Examples include:

Is it Working?

Our favorite all-in metric to measure the effectiveness of this strategy is the GTM Efficiency Ratio. This metric compares Net New Contracted ARR (CARR) in the quarter to the amount we spent on Sales & Marketing. In Q4 2024, we generated more than $4 of Net New CARR for each $1 spent on Sales & Marketing. By comparison, one analysis of public SaaS companies showed that the median company in Q3 2024 was generating $0.40 of Net New ARR for each $1 spent on Sales & Marketing.

PodPlay-GTM-Efficiency.png

Founder Led Sales at Scale

In the traditional B2B SaaS sales framework, founder-led sales gives way to a sales-led motion when product-market fit is achieved and a repeatable sales process established. At PodPlay we have chosen to use modern sales tools to double down on our founder-led motion. If our hypothesis proves correct, we can handle a massive increase in throughput while simultaneously increasing efficiency. 

As can be seen in the below table, in 2024 we were able to more than double our top of funnel throughput, while also more than doubling our win rate, and reducing our time-to-close by 75%.

PodPlay-Sales-Funnel-Stats.png

The formula to do founder-led sales at scale is: 

Insanely Great Product + Outlier Content + Modern AI Tools

The PodPlay Advantage

PodPlay gives venue operators all the tools they need to digitally manage a physical space - integrating video replays, automated scoreboards, and autonomous functionality with a reservation engine, event management, coach connect, membership module, and payments. 

Originally built to power PingPod, the network of futuristic autonomous ping pong clubs, PodPlay is now being used to manage venues across pickleball, padel, ping pong, golf simulators, racing simulators, soccer and pool, with more experience verticals to come in the future.

If you’re interested in learning more, request a demo.