Toby Hervey and the conversation before the conversation

Toby Hervey got a call from a friend who had fought with her boss. She wanted help deciding what to do next. He began doing what friends tend to do: taking her side. Then he caught the flaw in his own performance. Sympathy was plentiful. Useful distance was in shorter supply.

He sent her to Sarah Sheehan, a former colleague from Gilt Groupe whose judgment he already trusted. Sheehan helped the friend consider the other side of the exchange and work toward a resolution. A private favor had exposed a public problem: access to a sensible person was distributed rather unevenly.

Hervey and Sheehan founded Bravely in 2017 around that opening. Employees could talk confidentially with a professional coach before approaching the person at the center of a workplace problem. The company would eventually raise a $15 million Series A. Its starting point was considerably smaller: a friend, a phone call, and the recognition that loyal advice can be unhelpfully loyal.

A career with an unexpected loading dock

Hervey grew up in Florida and began helping at his family’s dog-grooming business at 11. The first business in his story had actual customers and very little patience for abstraction. Dogs, at least, are unlikely to be impressed by a mission statement.

He went north to Georgetown University, earning a bachelor’s degree in international politics. Government was once the plan; Secretary of State was an ambition. His eventual career would contain plenty of negotiations, although the route to them passed through a fashion warehouse.

At 22, he pursued conversations and introductions until he found an internship at Gilt. When the internship ended without a permanent opening, he took work cataloguing Gilt Man’s merchandise in the warehouse. He later moved to Gilt City and into strategy and business development. A first job can be an awkward fit. His solution was to find a way inside and keep moving.

His subsequent roles included Timehop and Waywire, the video startup associated with Cory Booker, before he joined Pager’s founding team in 2013. There he worked across operations, partnerships, and marketing. The résumé crosses consumer commerce, social products, and services. Running through it is the practical work of getting a new business into people’s lives.

Who gets someone in their corner?

Gilt also gave Hervey the relationship that mattered to Bravely’s beginnings. Sheehan had experience in HR and had become someone he could turn to himself. When he introduced his friend, he was drawing on a resource he already possessed. Building a company meant asking how that resource might become available to people outside his address book.

The distinction matters. Senior executives can be offered coaching as part of their development. A junior employee trying to prepare for a difficult conversation may have fewer places to go. An employer can announce a policy of openness without giving people much practice in being open.

Bravely sold access to employers, who made the service available to their employees. Its early model charged an access fee per employee. People could return to the same coach when an issue required another session. The arrangement made room for continuity without requiring every conversation to become a standing appointment.

There was a delicate piece of persuasion involved. HR leaders were both potential customers and people who might reasonably ask why employees needed an outside conversation. Hervey’s argument was that preparation could help people approach their colleagues and HR teams more productively. A pause outside the office could make the next conversation inside it easier to begin.

The pitch that went badly enough to help

Hervey’s own experience supplied a rather pointed demonstration. Early in fundraising, he met a friend from Gilt who had become a venture capitalist. He expected a friendly exchange about getting started. Instead, he got questions he could not answer well.

How large was the market? Where would the purchase fit into a company’s budget? What did approval look like? He left convinced the meeting had been dreadful. After calming down, he thanked his friend and recognized that he now had a useful list of questions to prepare for.

Two weeks later, the investor invited him back. The friend was Byron Ling at Primary Venture Partners, which led Bravely’s early funding round. It is a pleasingly uncomfortable origin for an investor relationship: the conversation Hervey disliked gave him something he needed.

That is also the tricky commercial proposition behind coaching. People often seek reassurance precisely when another perspective would serve them better. Building trust requires enough warmth to keep someone listening and enough honesty to make the listening worthwhile. Hervey had encountered the buyer’s version of his friend’s original problem.

Five days before the money

In 2019, a prospective Series A investor withdrew five days before closing. Hervey later acknowledged that Bravely had moved too quickly, attracted by the terms and round size. Primary’s Brad Svrluga helped organize existing investors into a financing note that gave the company time to continue.

By the next fundraising effort, preparation had become more deliberate. Cassie Young worked with the team on its commercial operation and took the board seat. A practice pitch to Primary brought another tough review. Hervey’s description of supportive investors was admirably economical: “It’s not summer camp.”

“It’s not summer camp.”

Toby Hervey, on honest investor relationships

The eventual announcement arrived in August 2021: $15 million, led by Telescope Partners. The company said employees were using Bravely in more than 68 countries and 33 languages. Those figures describe its reach at that moment, a long way from the original introduction between two friends.

The funding plans included expanding the coaching network and building a People Science function. At the time, Bravely’s customers included Autodesk, Nasdaq, Pinterest, Twilio, and Zillow Group. The ambition had become operational: making an individual conversation possible across different organizations, languages, and levels of seniority.

Inclusion after the confetti

Hervey’s interest in access extends beyond the company. He served on Out in Tech’s board and became its president; by 2021, public biographies described him as president emeritus. The organization connects the LGBTQ+ community in technology through professional relationships and opportunities.

In August 2017, he spoke at a Women in Tech rally hosted by Girls Who Code in Union Square. He credited women with giving him his first opportunity at Gilt when his qualifications were thin and his earnestness abundant. He also recognized their role in supporting gay rights. His argument for allyship began with debts he could name.

There is a revealing small detail in his account of the rally. Publishing the remarks afterward felt more nerve-racking to him than delivering them in a public square. Even a founder selling help with difficult conversations could find the written version intimidating. Confidence, apparently, does not arrive with a lifetime warranty.

In a June 2019 essay, he considered what remained after Pride decorations came down. Being openly gay at work informed his desire to create a company where people could be themselves and to help other employers do the same. Inclusion, in that account, required continuing attention to everyday behavior and to the different experiences employees bring to a workplace.

That perspective shaped Bravely’s intended audience. Hervey described reaching people earlier in their careers and groups that had traditionally received less access to coaching. The idea asked an employer to consider who already had support, who felt able to ask for it, and who might benefit from a quieter way in.

A benefit has to be used

In January 2019, Bravely offered hundreds of free coaching sessions in a New Year campaign. Hervey wrote that the sessions were claimed in less than a week. What interested him was the response from people choosing support at a moment when they wanted it. A calendar can announce that it is time for self-improvement. People tend to have their own schedules.

The practical questions remained visible as the business developed. At the 2019 ASU+GSV Summit, Hervey joined a discussion about scaling coaching alongside leaders including BetterUp co-founder Alexi Robichaux. Quality, the role of HR, and the implications of making coaching available across a team were all on the agenda. Wider access brings a longer list of responsibilities.

Hervey now leads partnerships at Granted. His current reflections on Bravely return to the distance between offering a resource and persuading someone to use it. Timing, a clear expected benefit, and ease of use matter. An announcement can tell employees that something exists; the product still has to earn their attention.

It is an appropriately practical place for his story to land. The former aspiring diplomat has spent years working on the steps that come before a useful exchange: an introduction, a rehearsal, a better question, a reason to trust the person across the table.

Bravely began when he noticed the limits of his own advice and knew whom to call. For all the money and machinery that followed, that remains a good scene to keep in view. A friend needed help. Hervey found someone better placed to give it. Then he began working out how more people could make that call.