Hey - Marc here.

Happy Saturday morning, motivated B2B SaaS Founders!

Here's at least one tip to keep in mind as you grow your B2B SaaS company:

Today's issue takes about 5 minutes to read.

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In today's issue, I share some key takeaways from Whale Boss’ CEO and founder Ryan Staley’s presentation at Nathan Latka's conference “SaaS Open 2023” in New York. He discussed how they hit $30m in ARR with only 4 sales reps in under 6 years.

Ryan created an enterprise team and grew it from $0 to $30m in ARR without lead generation, marketing support, and in a declining market. He closed over $125m in net new contracts and is a 19x award winner for Sales and Sales Leadership.

About Whale Boss

Whale Boss is a dynamic consultancy that prioritizes delivering rapid results over simply billing hours. They specialize in revenue sprints, enabling companies to swiftly implement scalable sales systems while retaining full ownership and control of their organization, without having to rely on external investors.

Ryan, the driving force behind Whale Boss, embarked on his entrepreneurial journey in 2000. He started as an inside sales representative, selling technology and providing training to CIOs, CTOs, and VPs within the world's largest investment banks and brokerages. He finished #1 nationally, leading to subsequent promotions as a Manager and Senior Manager.

After 2.5 years, Ryan took on a challenging role in a privately held managed services provider. With no existing customer base in the Chicago market, he executed a comprehensive go-to-market strategy, became a multi-year President’s Club winner, and earned equity within the organization.

This experience later launched Ryan into a leadership position at a new organization in which he was responsible for transforming a struggling business unit into a top-performing office, creating an enterprise team from scratch, and developing a recurring revenue engine.

PS With $30m in capital revenue, he secured over 30 contracts exceeding $500k each and landed a substantial $20m contract.

Challenges

His journey began with a failure.

Ryan initially experienced a failure of leadership. Eventually, he was promoted, which turned out to be a demotion in disguise. However, later on, he gained valuable insights that helped them elevate their enterprise team to a higher level.

Advice to Other Founders

Know your Annual Contract Value (ACV) and your average deal size.

When developing your go-to-market strategy, analyze your five biggest wins, five fastest wins, and five biggest losses. They discovered deals they should not have pursued, as well as deals that closed quickly that almost seemed like magic, or deals that have exceptionally large values.

Concept of "crawl, walk, run.”

They initially focused 80% on mid-market deals and 20% on larger enterprise deals then gradually shifted to 80-20 to identify the team members capable of selling enterprise deals while upskilling them without significant investment. Mid-size deals continued to come in while big hits started to stack on top.

Target specific niche events rather than taking a broad approach.

Sponsor such events, which may require a significant investment, but provide access to influential companies. Ryan was successful not only in being cost-effective with event sponsorship but also in building relationships with board members of these associations.

Leverage media as part of your strategy.

They believe that the future lies in the attention economy, where there is increasing competition and noise from various AI companies and software. They emphasize the need to stand out amidst the noise and using podcasts as a marketing tool.

TL;DR

Whale Boss, a consulting company, achieved $30M in ARR with only 4 sales reps. CEO Ryan Staley’s journey involved failures and promotions that led to valuable lessons. He emphasized understanding ACV and analyzing top wins, fastest wins, and biggest losses. They shifted focus from mid-market to enterprise deals gradually, targeted niche events, and built relationships with board members, resulting in cost-effective event sponsorships and access to influential companies. They also emphasized leveraging media, particularly podcasts, in the attention economy to cut through the noise. Whale Boss' achievements include $30m in capital revenue, securing large contracts, and successful business transformations.

PS Here is a link to the full interview if you are interested in listening to the full episode: How They Hit $30m in ARR with only 4 Sales Reps. in 5.5 years

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See you again next week.

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