Sameer Shariff on Building Cambly with Sustainable Growth

Sameer Shariff says Cambly grew from his and co-founder Kevin's experiences learning languages. He had studied Spanish at school without feeling proficient, but traveling alone in Argentina forced him to speak and gave him a much more rewarding way to practice.

Kevin had a similar experience with French. The two wanted a friendly person to practice with on demand, regardless of geography. They saw technology as a way to connect learners and speakers, then chose English because they believed it was the largest opportunity.

Shariff's first job after college was at Google, where he learned to build software at scale and worked on metrics and analytics. His team tested ideas rather than assuming that either person's intuition was right.

At a very early startup, however, there may be too little data for a meaningful test. Cambly tried halving its price when it was getting roughly one purchase a day; Shariff says there was no reliable way to measure the effect. Founders must initially understand the problem and use judgment.

Fundraising was difficult partly because Cambly's American founders were building for customers elsewhere. Investors who spoke English and knew mainly other English speakers had not experienced the problem themselves; previous struggles in language learning also made the sector harder to sell.

Stebbings challenges the business on the retention and low prices often associated with education apps. Shariff argues that one-on-one conversation and relationships with tutors create engagement and a social obligation to return. His explanation is a company perspective, not evidence of a measured causal effect.

Cambly had not experimented with fines for missed sessions, Shariff says. Its plans did, however, allocate minutes that could be lost if not used, encouraging the consistent practice he believes language learning requires.

Cambly's north-star measure was paid usage: the minutes students spend with tutors. Shariff prefers this to revenue alone because selling a promise and collecting upfront payment does not establish that customers actually use the service. Usage measures activity, though it does not by itself prove a learning outcome.

A difficult fundraising process forced the founders to work with limited resources. Shariff believes that taught them to build a more capital-efficient marketplace. He does not suggest every startup's fundraising or economics will follow the same path.

An attempted Series A did not go to plan, so the team switched to a plan for positive cash flow. Shariff says it reached that point about four months later and remained cash-flow positive through the interview. The account is his, and the interview does not independently audit the figures.

Cambly charged from the beginning because tutors had to be paid. During the push toward positive cash flow it adjusted pricing to improve its margin and offered longer commitments paid in advance. Upfront cash helped cash flow; it should not be confused with profit or revenue already earned.

The founders had also kept the team lean and taken on many roles themselves, a habit that preceded the crisis. Shariff says those earlier choices helped the company operate efficiently when a new financing round failed to materialize.

Stebbings says an investor told him Cambly had not touched its Series A or B money and asks whether it should spend more to grow. Shariff accepts the premise but says having a cash cushion changed the risks the company could take; he does not describe how individual dollars were held.

Shariff credits investors Jeremy Levine and Sarah Tavel with helping Cambly recruit and scale, alongside the value of the cash. He wants to grow as fast as possible while maintaining a healthy model rather than pursuing a milestone solely to raise the next round.

His concern is that a business burning heavily may learn growth tactics it cannot sustain. He frames the early years as experimentation to find mechanisms that could work over a much longer horizon, while acknowledging that his advice comes from his own experience.

When advising founders about funding, Shariff favors a lean operation, a strong core business and a path to standing on its own. His own optimism about an apparently promising raise proved unreliable, so he urges founders to consider what happens if financing does not arrive.

His idea of high performance has shifted from individual output toward leadership: helping a larger organization align around important outcomes. A manager's impact increasingly depends on how effectively the wider team can act.

Adding people does not automatically preserve speed. Shariff says planning, shared goals, clear ownership and autonomy become more important as a company grows, though he describes Cambly's own approach as a continuing learning process rather than a solved formula.

The failed Series A was a formative leadership experience. Shariff describes it as an existential risk at the time: the founders were focused on preserving cash, while colleagues, unaware of that context, were still working on valuable longer-term growth projects.

The founders decided to tell the whole company that the raise had failed. Shariff feared employees might lose confidence or leave, but concluded that the team needed the information to help solve the problem.

They presented a plan and evidence that some pricing changes were already improving gross profit, instead of simply announcing bad news. Shariff recalls the team leaving the meeting aligned on the work needed to reach a sustainable position.

That discussion happened in person. Shariff prefers in-person collaboration, but says the company later held a similarly open conversation over video when the pandemic began, and in his view achieved alignment remotely as well.

Shariff likes immersive learning and first-principles thinking: he wants to understand why an idea works, not just what someone recommends. Stebbings describes his own different method of speaking to knowledgeable people, comparing their answers and then researching the recurring themes.

Shariff also learns by applying concepts. As a student he used calculus to think about a bike ramp; accounting became more compelling when Cambly's business depended on it. The need to solve a real problem made the subject more engaging.

His fastest learning, he says, has often come from one-on-one conversations with an expert, where he can focus on the edge of what he knows. That preference is also central to Cambly's commercial model.

Shariff invokes the historical Bloom two-sigma research on individual tutoring and says Cambly is attempting to bring one-on-one learning to a much larger market. The interview supplies no comparable outcome study of Cambly itself, so the historical finding should not be treated as proof of its product's effectiveness.

Shariff describes Cambly as a demand-constrained marketplace: acquiring students cost-effectively is the bottleneck. Early tutors came from job boards and forums; he says referrals later contributed and the company onboarded tutors in step with student demand.

For product marketing, he favors stories about people and specific details over abstract categories. He recounts a Turkish pilot who used Cambly to work toward flying internationally, making the practical motivation for learning English memorable.

Experienced leaders can make the CEO's job easier by taking responsibility for domains they know better. At the same time, a larger customer base and team raise the stakes, and it becomes harder to transmit culture through individual relationships alone.

Shariff worries that an expanding organization may not move any faster, making it less efficient even if its absolute pace stays the same. He says maintaining or increasing velocity as headcount grows has been a learning curve.

Cambly's first employee was a Korea country manager, an unusual hire for two software engineers but useful because the founders lacked local language and cultural knowledge. Shariff says Korea soon became its largest market after that hire.

A strong individual marketer does not necessarily make a strong manager. Shariff says some country-manager hires struggled to build teams or with analytical work, and he learned to assess both capabilities and correct hiring mistakes promptly.

When looking for potential managers, he values interest in leading, understanding what motivates people, self-awareness and humility. He recalls underestimating how difficult management would be and emphasizes openness to learning.

Shariff describes himself as open to risk but careful about understanding decisions. Leaving a comfortable Google role to start Cambly was a substantial professional risk; in personal life he also enjoys activities such as skydiving and skiing.

His book choice is The Most Human Human by Brian Christian, whom he identifies as a close friend. The book's exploration of human connection and the Turing test appeals to him in part because of its parallels with Cambly's one-on-one interactions.

He sees delegation and granting autonomy as strengths: country managers received broad objectives and room to decide how to reach them. A corresponding weakness is his tendency to think decisions through carefully when a startup must move with incomplete information.

To counter that tendency, he relies on people with different styles, including his co-founder, and seeks advice that can accelerate a decision. He says connecting a global workforce and preserving and evolving the culture are among his hardest current challenges.

Asked which other company he would lead, Shariff chooses Airbnb. He admires its cross-border marketplace, the new behavior it introduced and its role in connecting people in different places.

Looking back, he wishes Cambly had hired experienced leaders earlier instead of learning so much on the job. He cites senior hires from Airbnb Experiences and Pinterest as examples of expertise that can help a company move faster.

He would like more people to have access to information and education about startups. His own route through Google, another startup and Y Combinator gave him contacts from whom he could learn, an advantage he recognizes is not universal.

Asked in 2022 to imagine 2027, Shariff says Cambly's mission is to make high-quality English learning accessible to far more people. He sees affordability and better matching between students and tutors as concrete areas of work, not completed results.

For example, Shariff says the Turkish pilot found a tutor with aviation experience and could practice language relevant to air traffic control. He hopes better matching will connect each student with a tutor suited to their individual needs.

Personally, he wants to keep learning and become a better leader as the company grows. The interview closes with his enthusiasm for the new challenges of running a startup and Stebbings thanking him for the conversation.