Strategic Account Executive, Headout
Dex
$175-275k
OTE
+ Equity
3 days a week in office
Travel experiences marketplace
Posted today
Travel experiences marketplace
501-1000 employees
Posted today
$175-275k
OTE
+ Equity
3 days a week in office
501-1000 employees
Company mission
Headout is on a mission to make travelling more fun & spontaneous.
Role
Who you are
- You've closed, consultatively and end-to-end. You bring 5–8 years of enterprise sales experience and a strong quota-carrying track record of closing meaningful, consultative deals - owning the full cycle from first touch to signature
- You've built from zero. You've sold something new before, launched a product, opened a market, or created demand where none existed and you know how to build pipeline, playbooks, and process without waiting for someone to hand them to you
- You bring structure to ambiguity. You think strategically, prioritize well under competing demands, and bring clarity to situations where the path isn't defined
- You collaborate across functions. You work well with product, operations, marketing, and leadership teams to execute sales initiatives end-to-end
- A strong plus: Deep fluency with AI tools and the credibility to sell an AI product with real depth. You don't need to be an engineer but genuine curiosity about and daily use of AI will accelerate everything you do here
- Good to have: experience selling into governments, universities, public institutions, or non-profits
What the job involves
- Dex is Headout's AI-powered travel companion that transforms how visitors experience the world's most iconic venues. It's a new kind of product in a market that doesn't have a playbook yet, and we're looking for a Strategic Account Executive in New York to take it to market and own net-new revenue from day one
- You'll own the full sales lifecycle — identifying and pitching opportunities, closing deals, and growing long-term relationships, while helping define the commercial playbook a category-creation product deserves
- This is a highly entrepreneurial role suited for someone who enjoys building new business lines, navigating ambiguity, and operating with high ownership in a fast-moving environment. You'll report directly to the GM, North America
- Build from 0→1: You'll be the founding commercial hire for Dex, helping define the commercial playbook, partnership strategy, and expansion opportunities from the ground up
- Own both acquisition and growth: You'll drive the full sales lifecycle, from outbound prospecting and commercial negotiations to account management and long-term growth
- Define the category: Dex isn't another product in a crowded market. You'll create the need and educate buyers on a genuinely new kind of experience, rather than respond to existing demand
- Operate globally: You'll work across international markets and collaborate closely with teams across product, growth, operations, and leadership
- High ownership, direct to leadership: Reporting to the GM, North America, you'll have significant autonomy, direct exposure to leadership, and the opportunity to shape how Dex evolves commercially
Our take
Over 25 million people from over 105 different cities have purchased a ticket for something on Headout, the mobile-first travel experience and activity platform. It’s a digital marketplace where users can browse tickets to leisure activities in their area, and providers can in turn get help filling last-minute slots.
Unlike some travel and hospitality businesses, Headout has already bounced back and surpassed its pre-pandemic revenue (3.1 Yx oY) and growth (3.2 x YoY) levels. The key was to focus on domestic travel, a new vertical it intends to expand in future with new funding on the table. It’s also looking to aggressively grow its footprint to add hundreds of new cities over the coming years, having doubled its business team in 2023.
Headout is in a very comfortable position to do so: every transaction it carries out is profitable, and there’s plenty of runway on its current funding. This means the team can focus on building out new features for both users and providers. The quality of its product will be its key advantage over Airbnb, which has for a while now been developing a competing marketplace.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Company
Funding (last 2 of 5 rounds)
Feb 2022
$30m
SERIES B
Sep 2021
$12m
SERIES B
Total funding: $65.7m
Company benefits
- Unlimited mental wellness leaves
- No ceiling general leave
- Every quarterly 1-1 includes a `vacation time` item on the agenda to ensure everyone takes breaks proactively
- 50% off fitness class memberships
- Wellness programs once a month
- Online health platform(s) subscriptions
- Employee Assistance Program. We've got your back
- $500 `Headout Credits` to, you guessed it, head out to any of our experiences around the world
- Unlimited `Learning Credits` for paid courses and sessions to aid your learning & growth
- Access to conferences and meet-ups
- Community Lunches twice a week across all offices
- Travel across our 6 global offices if your role demands it
- If your role requires you to move countries, we will do whatever it takes to take care of you. We are not limited by any policies when it comes to getting great talent to join us
- ESOPS: We follow the standard 1-year cliff and 4-year vesting schedule. You can exercise your ESOPs anytime up to 2 years post-termination. For employees who have been at Headout for a continuous period of 2 years or longer, the exercise period will automatically extend to the life of the option i.e. **10 years**.
- Outside of teams that are remote-first, everyone else will be expected to spend **50% of their time in the office**. 50% doesn't mean spending 2.5 days a week at the office. It is entirely up to the individual and the team to configure what works best for them
- Non-remote teams will have complete flexibility to **work from anywhere** for extended durations multiple times a year. Longing to work from a beach for a couple of weeks, no problem
- You can access any of our hub offices at any time
- Everyone gets a one-time allowance of up to **$250** to set up a productive work environment for themselves outside of the office
Company values
- 👉 Headout > I
- 👉 Move fast, learn faster
- 👉 High standards
- 👉 Together is better
- 👉 Take ownership and initiative
Company HQ
Midtown South, New York, NY
Leadership
Varun Khona
(CEO)Previously founded and served as CEO of travel company Trippy.
Vikram Jit Singh
(CTO)Previously a senior member of the technical staff at Oracle.
Suren Sultania
(COO)Worked a spell as a consultant at PTOLEMUS Consulting Group.
Salary benchmarks
We don't have enough data yet to provide salary benchmarks for this role.
Submit your salary to help other candidates with crowdsourced salary estimates.
Share this job
View 2 more jobs at Headout