Coaching platform Leland has raised $12 million in Series A funding led by Forerunner Ventures with participation from GSV ventures to grow its platform geared toward matching coaches and aspirants to fulfill goals ranging from getting into a university to passing an entrance exam and excelling at product management. The company aims to build better tools for coaches to create content and manage their schedules, as well as build out its enterprise offering.
The startup was founded in 2021 by John Koelliker, a former product manager at marketplaces including Uber and LinkedIn. It has raised $17.1 million in funding to date, with investors including Goodwater, FJ Labs, Next Play Ventures, and a few LinkedIn executives.
Since the company raised its last round in 2022, it has experienced steady growth, with its revenue increasing fourfold in the past year. The company said it had conducted over 50,000 coaching sessions on the platform in the last 12 months. Leland currently has more than 100,000 users from 70 countries who are accessing coaching, courses, and events.
Koelliker noted that the company didn’t need to raise the money as it was cashflow positive. However, it raised funds because the business was hitting an inflection point. The startup felt it had to invest more to grow.
Building a strong coaching supply
The platform has more than 1,000 coaches across different categories. The startup says most of these coaches come to them organically after a friend or a family member tells them about the platform.
“We still have 75% organic growth because there is so much sharing within friends, family, and users’ networks. One of the counterintuitive things with Leland is that we have everything from dental school admission to software engineering coaching. While these are different paths, coaches in different sectors are often tightly networked, and that helps us build a strong supply and discovery side,” Koelliker said.
The company structures the onboarding process for coaches to ensure they clearly identify their areas of expertise. It also sends a vouch link to new coaches so people in their network can affirm that the coach has expertise in a certain segment.
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San Francisco | October 27-29, 2025 REGISTER NOWWhile the platform’s core pitch is its network of coaches, it also has courses and events where people can take part in groups. Koelliker noted that Leland vets the supply of coaches strictly and has only a 5% acceptance rate to ensure that the platform only gets high-quality coaches.
B2B tools for coaches
Since raising its seed round, Leland has thought about building management tools for coaches, including better payments, messaging, scheduling, CRM, time tracking, reviews, and discount codes. The company thinks these tools can help coaches better monetize their expertise. The startup calls this tooling “business in a box” for coaches.
The company also offers an AI-powered tool for coaches that provides them with session summaries, action items, and key takeaways akin to meeting-intelligence tools like Read AI and Otter.
“We have tried to make packages and templates that coaches can use to slot their expertise and content. This makes onboarding easier for coaches and discovery better for users,” Koelliker said.
During onboarding, the platform uses AI to take a gist of a coach’s work experience and suggest attractive headlines and bios for their Leland profiles.
Product roadmap and future opportunity
Koelliker noted that a lot of Fortune 500 companies offer Leland’s services and coaching sessions as a perk to their employees. The startup wants to bank on that and invest in its enterprise tooling to expand that area of business more.
The company is also experimenting with an AI-powered onboarding tool for end customers, who can describe their goals and get suggestions for appropriate coaches for those goals. What’s more, the startup is expanding the category of goals and coaches to reach a broader audience. It plans to use AI to help coaches develop interactive coaches adapted to a learner’s progress.
Eurie Kim, managing partner at Forerunner Ventures, said that, as a firm that invests in consumer tech, it wanted to invest in the area of career advancement and coaching for the longest time.
“We’re seeing younger generations deeply struggle to find purpose and direction in young adulthood, all while the job market becomes increasingly competitive and higher ed all the more expensive. Alongside this, AI has a clear opportunity to reshape how people learn, transforming what’s possible with personalization and efficiency,” she said.
Kim emphasized that Leland’s model of creating a marketplace with top-quality coaches, along with reviews and hands-on support, creates an opportunity for the startup to grow.
“Coaches benefit from advanced tools for running their business: built-in marketing, simplified back-end processing, and AI features for scale and efficiency. The referrals and organic growth that Leland is seeing already demonstrate network effects at work,” Kim added.
Leland competes in a tough market with other startups, like executive coaching company BetterUp; a16z-backed Intro, which connects high-profile experts to builders and founders; AceUp, which provides workplace coaching; Shimmer, a coaching platform for people with ADHD; and group-focused coaching company HumanQ.