Innovation Blog

Turbulence is Part of the Founder Journey: Interview with Daniel Senyard, Alumni-in-Residence


Daniel Senyard, CEO of travel tech startup, Shep, is joining the MassChallenge Texas in Austin 2020 cohort as an Alumni-in-Residence. Daniel participated as a founder in the inaugural MCTX Austin cohort. He grew up in South Africa, met his wife in London, and has lived in Santa Barbara, Seattle, Austin, and briefly in New Delhi for a travel startup he worked for. In this Q&A, Daniel recounts some of the learnings he’s picked up along his journey as a serial entrepreneur, as well as words of advice to this year’s MCTX Austin cohort on how to make the most of their experience this summer.


Q: Tell me about your startup.

A: Our team here at Shep works on optimizing the business air travel booking process.  For many large companies, about 30% of air travel bookings occur in a blind spot. That is, an increasing number of these companies’ employees are no longer booking their business travel through company travel policies because of a lack of usability. This results in employers being unable to control their spending because they can’t see the booking transaction. Shep addresses these pain points through a web browser plug-in that allows employees to make their own bookings, provides real-time guidance to book according to company guidelines, and reports booking outcomes to employers. Our name comes from the goal of shepherding our users to comply with company policies without a headache.

DanielSenyard-ShepTravel-2-250 (1)

Q: What has the growth of the company looked like?

A: We started in 2016 and spent about a year-and-a-half building, then raised several rounds with strategic investors from HomeAway, Flight Centre, Sabre, and Travelocity Business. A huge win came in 2018 when Shep was voted the winner at the Plug and Play Travel Demo Day by Silicon Valley VCs, angel investors, and travel industry experts. We are currently in pilot with several Fortune 500 companies and have a reseller partnership with Flight Centre, one of the world’s top four corporate travel agencies.


Q: How does your background connect to your current work?

A: I founded my first company in 2011 and it was in the music consumer space. The core technology allowed bands to display fans photos in a live visual installation at the concert. Then Instagram came out and we couldn’t keep up. I then joined a new travel startup as Chief Product Officer. I was there for 3 years and we got investment from a big travel company named Amadeus. Then I moved out to New Delhi with my wife and kids, trying to make the partnership work. That was where I got into the meat of the travel tech industry. I really got to see what problems people were trying to solve, and I think the ability I gained from being a copy and techincal writer to empathize with people and synthesize information led us towards more innovative solutions. Big companies wanted data, control, and savings and they assumed that they had to close people into a single booking environment to get those things. I figured that if we could shepherd behavior through a ubiquitous browser extension, then we could solve the problem with a decentralized solution that retained employee independence and provided data, control, and savings to employers.

Q: What was your experience with MassChallenge like?

A: Shep was accepted as part of the first MassChallenge Texas cohort, so we got to see the budding stage of the programming. I had gone through a few accelerator programs before MassChallenge, and the experience was unique because of the genuine sense of community that’s developed amongst the founders. My favorite memory is when we all got out of the co-working space and had a picnic outside. Just kicking the ball around with other folks, laughing, and talking about our ideas was such a wonderful moment of camaraderie amongst us. To this day, I feel that there’s a lot of romanticism surrounding entrepreneurship and raising large rounds, but the reality of the day-to-day has its ups and downs. Having access to other people who are going through that journey in parallel with yours is something I still draw value from today.


Q: As an incoming Alumni-in-Residence, what impact would you like to have on this year’s cohort of founders?

A: I’m looking forward to getting to know everyone and really want to recreate that sense of “kicking the ball around” type of community I enjoyed during my cohort. I’ve been talking with Natalie (link) about the sorts of events we can host to promote building connections, so look forward to that! For this year’s founders, I’d like to extend the advice that this opportunity to make connections is unlike any other and to take advantage of it. As I’ve found to be the case with Shep, I want to continue to listen and empathize with founders as they navigate through their parallel journeys. Excited to meet you all!


New to MassChallenge?

Visit the Join section of our site to learn more about the organization and how you may benefit by getting involved.

Upcoming events