Conversation with Kevin Wagstaff, (exited) co-founder of Spectora, investor, and advisor

Come for a live expert session with Kevin Wagstaff, co-founder of Spectora — a bootstrapped SaaS that grew to $15M in ARR serving the home inspection industry. Kevin did it all: founder-led sales, SEO and content, product design, customer success — and eventually helped lead the company through hiring a CEO and selling a chunk to private equity.

We’ll dig into what it really took to grow the company, the lessons learned along the way, and how he navigated the transition from founder-operator to board member.

Here’s what to expect:

• 30 minutes of interview-style conversation covering growth, founder mindset, and the PE deal.
• 30 minutes of open Q&A — ask Kevin anything about scaling, selling, or staying scrappy.

Introduction to Kevin and Spectora

Tracy introduced Kevin as a mentor with a background in building Spectora, a home inspection software company. She explained the format of the call, emphasizing that the first half would consist of questions directed at Kevin, followed by an open Q&A session.

Inception of Spectora

Kevin shared the origin story of Spectora, explaining that the idea emerged from his experience as a realtor and a friend's suggestion. He identified a gap in the market for home inspection reports, which were often lengthy and unhelpful. This led to the development of a modern SaaS solution for home inspectors.

Early Go-to-Market Strategy

Kevin described his initial approach to market entry, which involved direct engagement with potential customers through coffee meetings and customer interviews. He emphasized the importance of understanding customer workflows and pain points to tailor the product effectively.

SEO and Content Strategy

Kevin discussed his early focus on SEO, creating valuable content, and leveraging YouTube and podcasts to educate home inspectors. He highlighted the importance of being useful and helpful to rank well in search engines and attract customers.

Growth from $1 Million to $15 Million ARR

The conversation shifted to the strategies employed to grow Spectora from $1 million to $15 million in annual recurring revenue (ARR). Kevin mentioned the shift towards partnerships, affiliate marketing, and attending industry conferences to build relationships and trust.

Hiring and Team Structure

Kevin shared insights into the hiring process, noting the challenges of transitioning from founder-led sales to a more structured sales team. He discussed the importance of separating roles for inbound and outbound sales and the difficulties faced in hiring the right talent.

Challenges with Churn

The topic of customer churn was addressed, with Kevin explaining that the high churn rate was largely due to the nature of the home inspection industry, where many inspectors fail within their first year. He emphasized the need for a strong understanding of customer needs to mitigate churn.

Private Equity Involvement

Kevin detailed his experience with private equity, explaining the decision-making process behind selling a minority stake in Spectora. He discussed the importance of building relationships with potential investors well before considering an exit.

Cultural and Organizational Challenges

The conversation touched on the cultural shifts that occurred as the company grew, particularly around the 30-employee mark. Kevin emphasized the need for clear communication and alignment of goals across teams to maintain a strong company culture.

Meeting Structures and Communication

Kevin outlined the meeting structures that were implemented, including weekly all-hands meetings and one-on-ones with direct reports. He highlighted the importance of celebrating wins and maintaining transparency about customer pain points.