Sarah Sheehan and the art of asking anyway

Sarah Sheehan worked in human resources when she decided she wanted a sales job. More precisely, she wanted to help launch Gilt City, a new business inside the company where she already worked. She took the idea to Kevin Ryan, Gilt’s founder and chairman. He gave her a chance. A few years later, she was leading 65 salespeople and carrying responsibility for $60 million in revenue. The first sale had been herself.

That move provides a useful introduction to the co-founder and CEO of Bravely. Her business connects employees with professional coaching, including people who would once have needed a much grander title to qualify. Her own career contains an argument for the service: sometimes the gap between the job you have and the work you could do begins with a conversation you have yet to start.

Sheehan has called herself a late bloomer. There is something pleasingly uncooperative about that description when set beside a 65-person sales operation. It suggests she measures progress against an internal timetable, one that a respectable revenue number cannot quite persuade to behave.

The first sale was permission

Before entrepreneurship, there was a substantial apprenticeship in how companies work. Sheehan held HR roles at Sirius, Coach, and Gilt Groupe. These were different businesses, but each put her close to the bargains people make with their employers: what they expect, what they accept, and what they find difficult to say.

Gilt brought a different education. Moving into sales gave her responsibility for a team’s commercial performance. She could see how unresolved problems between employees and managers affected the work. A conversation deferred did not disappear simply because a revenue target had arrived. People still had to collaborate, make decisions, and trust one another enough to get things done.

She later co-founded Junior Explorers, an education venture that joined the 500 Startups accelerator. The sequence matters. Bravely emerged after experience in HR, sales management, and an earlier startup. Sheehan had already tried changing professional lanes and building a business before she and former Gilt colleague Toby Hervey started it in 2017.

Friends and colleagues were also bringing her their career questions. Eventually, introductions extended the circle to strangers. Advice had become a recurring request before it became a company offering. There is a modest but revealing distinction here: people were choosing her as someone to call, without a benefits portal telling them to.

A company for the conversation before the conversation

Hervey had encountered the same need from another direction. A friend called after a difficult exchange with her boss, uncertain about what to do next. Should she look for another job? Raise the issue internally? First, she needed someone to help her think. The founders saw room for a service between private confusion and a consequential workplace decision.

The early Bravely proposition was confidential, off-the-record coaching. Employees could talk through a problem with someone outside their immediate chain of command. The employer would make the resource available; the employee would have room to prepare. That arrangement addressed a familiar hesitation: asking the person involved in a problem to be your first adviser about it can require considerable optimism.

Sheehan brought experience from both sides of the HR desk and the sales target. Hervey brought a different set of operating experience. They had known each other through Gilt, and Sheehan described their strengths as complementary. She also made a specific point about fundraising: her relationships had helped secure introductions to investors. Her contribution was part of the company’s ability to get started.

New York suited that ambition. Sheehan valued the city’s mix of industries, which gave the founders potential customers beyond the technology sector. The underlying difficulty could occur in many kinds of company. A performance review, an awkward conversation with a manager, or an uncertain next step did not require a startup address.

Employee number one at the listening end

Sheehan was Bravely’s first coach, known inside the service as a Pro. She used her HR and team leadership experience to help develop its methodology and worked with employees at the earliest client companies. Then the demands of building Bravely pulled her toward running the business.

More than two years later, she stepped in at short notice to cover a coaching session. Some colleagues had never seen her do that part of the job. The employee was unsure the session would be useful. As they talked, a problem emerged: the employee had new responsibilities and was being pushed toward a leadership style they did not admire.

Sheehan saw empathy, integrity, and self-awareness in someone who had been told they were falling short. The employee decided to step back from the new responsibilities. The encounter challenged the assumption that progress always means taking on more. A coach, too, could leave a conversation having reconsidered what good leadership looked like.

The ladder meets the living room

Becoming a parent brought another revision. In 2020, Sheehan wrote about the difficulty of combining her work with caring for her young daughter, Mabel. She had spent years prioritizing professional advancement. Now the daily requirements of family life made it harder to maintain the appearance that every commitment could fit neatly around work.

She began allowing her daughter into video meetings and setting clearer boundaries on her time. She also became more willing to acknowledge difficulty in front of colleagues. These were practical changes to how she led. An employee listening to a founder discuss her own limits receives a different invitation from one hearing an abstract endorsement of openness.

Her work had long involved helping other people account for their circumstances. Applying that generosity to herself required a further adjustment. The tension gives her advocacy some texture: she was learning to use the same permission she wanted employees to have. Even the person who helps build the coaching service can need reminding.

Who gets a coach?

There had been an earlier experiment in opening the door. In January 2019, Bravely offered the first 365 people who signed up a free, 45-minute coaching call. The campaign, which has since ended, briefly let individuals try a service ordinarily purchased by their employers. The company invited people to consider opportunities in the jobs they already had, including what a colleague might teach them or a conversation might resolve. For a business selling to organizations, it was a way to put the experience directly into an employee’s hands.

In August 2021, Bravely announced a $15 million Series A led by Telescope Partners. The company said employees were using its service in more than 68 countries and 33 languages. Those were figures from that moment, when Sheehan was president and Hervey was CEO. Today, Sheehan leads the company as CEO.

The investment supported an ambition that remains central to her work: extending development beyond the executive ranks. Bravely’s network could help an employee prepare for a difficult exchange or set priorities without waiting for promotion into the small group traditionally offered individual coaching. Customers named at the funding announcement included Autodesk, Flexport, and The New York Times.

For Sheehan, access also involves who someone can choose to speak with. She has described Bravely’s identity-matching feature, which lets employees seek a coach sharing up to two identity markers, such as gender or race. She connects that choice to her own preference for discussing some leadership questions with women who understand aspects of her experience.

Her emphasis is specific. Making a service available is one decision; making an employee comfortable using it is another. In a 2024 conversation with leadership coach Andrew Tallents, equitable access and support for underrepresented employees remained part of her stated mission. The question of who gets development has followed her from the founding idea into the CEO role.

Even the CEO needs someone to call

Sheehan’s own circle includes Sara Patterson, her first boss, whom she credits with generosity and direct feedback. Another is fellow founder Esther Park of Nara Organics. Sheehan has described daily calls with Park about running companies, with humor forming part of the exchange. The founder of a coaching company still has people she turns to.

“Be bolder, sooner.”

Sarah Sheehan, on advice to her younger self

That short instruction fits her career. Asking to launch Gilt City came before she had the sales leadership record that would make the request look obvious in retrospect. Building Bravely required another decision to move before certainty arrived. Experience can make an earlier leap look orderly; at the time, someone still has to ask.

A new tool, the same unfinished question

In July 2025, Sheehan set out her view of AI’s role in coaching. She saw possibilities for more timely support and broader access to development, while preserving a place for human connection. Bravely’s current offering combines human coaching with technology intended to help people learn during their everyday work.

By May 2026, her public agenda also included The Steady Leader, a webinar for HR and People teams about helping managers lead through change. The program’s premise was practical: managers need a way to remain consistent as demands shift around them. For a founder whose career has crossed functions and business models, change is familiar territory.

The connecting thread is the next conversation. Sheehan once needed to persuade a founder that an HR professional could help build a sales business. Employees using Bravely may need to ask for feedback, question an expectation, or decide what they want from a role. Her company has grown around making room for that preparation. The meeting still belongs to the person walking into it.