Strategic Account Executive, Dex

🚀 Why Headout?

We’re a rocketship: 9-figure revenue, record growth, and profitable

With $200M in revenue, guests in 700 cities, and 18 months of profitability, Headout is the fastest-growing marketplace in the travel industry, and we’re just getting started. We've raised $60M from top-tier investors and are building a durable company for the long term — because that's what our mission needs and deserves. We’re growing, profitable and nowhere near done.

What we do is important

In an increasingly digital world, there is a desperate need to augment our human experience by getting us to interact with the real world around us and the people in it. At Headout, our mission is to be the easiest, fastest, and most delightful way to head out to a real-life experience — from immersive tours to museums to live events and everything in between.

Why now?

The foundation is strong. The opportunity ahead is even bigger. We’ve hit profitability, built momentum, and proven the model — but there’s so much more to build. If you’re looking to join a company where the trajectory is steep and your impact is real, this is the moment.

Our culture

Reinventing the travel industry isn't easy, but that's the fun part.

We care deeply about ownership, craft, and impact, and we’re here to do the best work of our careers. We won’t pretend like it’s for everyone but if you’re a builder who loves solving tough problems, you’ll feel right at home.

👩‍💻The role

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.

🤩What makes this role special?

• 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.
  
  

🎯You are a great fit if

• 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.
  
  

🚫You are not a great fit if

• You need an established playbook. There's no inbound engine, no battle-tested pitch deck, and no predecessor to learn from. If you do your best work inside a mature team, this role might not be the right fit.
• You prefer to sell into existing demand. Buyers don't know they need Dex yet. If educating the market and helping create a category doesn’t excite you, this probably isn’t the role for you.
• You want a narrowly-scoped closing role. You'll prospect, pitch, negotiate, close, and manage accounts, all of it.
• Ambiguity slows you down. Priorities will shift as we learn. If you need certainty before you can move, the pace here won't suit you.
  
  

This role has an on-target earnings (OTE) range of $175,000 – $275,000, based on the candidate's experience. You will also receive equity through our ESOP program.

➕Benefits

• Health insurance including dental and vision.
• Hybrid work schedule, including 3 days per week in our NYC office.
• $250 to set up a productive work environment outside of the office.
• $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.
• Travel across our 9 global offices if your role demands it.
  
  

EEO statement

At Headout, we don’t just accept differences — we celebrate it, we support it, and we thrive on it for the benefit of our employees, our partners, and the community at large. Headout provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age or disability. During the interview process, if you need assistance or an accommodation due to a disability, you may contact the recruiter assigned to your application or email us at life@headout.com.

Privacy policy

Please note that once you apply for this job profile your personal data will be retained for a period of one (1) year. Headout shall process this data for recruitment purposes only. Once the relevant job profile is filled or once the time period of one (1) year from the date of the job application has passed, whichever is later, Headout shall either delete your data or inform you that it shall keep it in its database for future roles. In compliance with the relevant privacy laws, you have the right to request access to your personal data, to request that your personal data be rectified or erased, and to request that the processing of your personal data be restricted. If you have any concerns or questions about the way Headout handle your data, you can contact our Data Protection Officer for more information.

244 results found

No results found

• Afghanistan 93
• Åland Islands 358
• Albania 355
• Algeria 213
• American Samoa 1
• Andorra 376
• Angola 244
• Anguilla 1
• Antigua & Barbuda 1
• Argentina 54
• Armenia 374
• Aruba 297
• Ascension Island 247
• Australia 61
• Austria 43
• Azerbaijan 994
• Bahamas 1
• Bahrain 973
• Bangladesh 880
• Barbados 1
• Belarus 375
• Belgium 32
• Belize 501
• Benin 229
• Bermuda 1
• Bhutan 975
• Bolivia 591
• Bosnia & Herzegovina 387
• Botswana 267
• Brazil 55
• British Indian Ocean Territory 246
• British Virgin Islands 1
• Brunei 673
• Bulgaria 359
• Burkina Faso 226
• Burundi 257
• Cambodia 855
• Cameroon 237
• Canada 1
• Cape Verde 238
• Caribbean Netherlands 599
• Cayman Islands 1
• Central African Republic 236
• Chad 235
• Chile 56
• China 86
• Christmas Island 61
• Cocos (Keeling) Islands 61
• Colombia 57
• Comoros 269
• Congo - Brazzaville 242
• Congo - Kinshasa 243
• Cook Islands 682
• Costa Rica 506
• Côte d’Ivoire 225
• Croatia 385
• Cuba 53
• Curaçao 599
• Cyprus 357
• Czechia 420
• Denmark 45
• Djibouti 253
• Dominica 1
• Dominican Republic 1
• Ecuador 593
• Egypt 20
• El Salvador 503
• Equatorial Guinea 240
• Eritrea 291
• Estonia 372
• Eswatini 268
• Ethiopia 251
• Falkland Islands 500
• Faroe Islands 298
• Fiji 679
• Finland 358
• France 33
• French Guiana 594
• French Polynesia 689
• Gabon 241
• Gambia 220
• Georgia 995
• Germany 49
• Ghana 233
• Gibraltar 350
• Greece 30
• Greenland 299
• Grenada 1
• Guadeloupe 590
• Guam 1
• Guatemala 502
• Guernsey 44
• Guinea 224
• Guinea-Bissau 245
• Guyana 592
• Haiti 509
• Honduras 504
• Hong Kong SAR China 852
• Hungary 36
• Iceland 354
• India 91
• Indonesia 62
• Iran 98
• Iraq 964
• Ireland 353
• Isle of Man 44
• Israel 972
• Italy 39
• Jamaica 1
• Japan 81
• Jersey 44
• Jordan 962
• Kazakhstan 7
• Kenya 254
• Kiribati 686
• Kosovo 383
• Kuwait 965
• Kyrgyzstan 996
• Laos 856
• Latvia 371
• Lebanon 961
• Lesotho 266
• Liberia 231
• Libya 218
• Liechtenstein 423
• Lithuania 370
• Luxembourg 352
• Macao SAR China 853
• Madagascar 261
• Malawi 265
• Malaysia 60
• Maldives 960
• Mali 223
• Malta 356
• Marshall Islands 692
• Martinique 596
• Mauritania 222
• Mauritius 230
• Mayotte 262
• Mexico 52
• Micronesia 691
• Moldova 373
• Monaco 377
• Mongolia 976
• Montenegro 382
• Montserrat 1
• Morocco 212
• Mozambique 258
• Myanmar (Burma) 95
• Namibia 264
• Nauru 674
• Nepal 977
• Netherlands 31
• New Caledonia 687
• New Zealand 64
• Nicaragua 505
• Niger 227
• Nigeria 234
• Niue 683
• Norfolk Island 672
• North Korea 850
• North Macedonia 389
• Northern Mariana Islands 1
• Norway 47
• Oman 968
• Pakistan 92
• Palau 680
• Palestinian Territories 970
• Panama 507
• Papua New Guinea 675
• Paraguay 595
• Peru 51
• Philippines 63
• Poland 48
• Portugal 351
• Puerto Rico 1
• Qatar 974
• Réunion 262
• Romania 40
• Russia 7
• Rwanda 250
• Samoa 685
• San Marino 378
• São Tomé & Príncipe 239
• Saudi Arabia 966
• Senegal 221
• Serbia 381
• Seychelles 248
• Sierra Leone 232
• Singapore 65
• Sint Maarten 1
• Slovakia 421
• Slovenia 386
• Solomon Islands 677
• Somalia 252
• South Africa 27
• South Korea 82
• South Sudan 211
• Spain 34
• Sri Lanka 94
• St. Barthélemy 590
• St. Helena 290
• St. Kitts & Nevis 1
• St. Lucia 1
• St. Martin 590
• St. Pierre & Miquelon 508
• St. Vincent & Grenadines 1
• Sudan 249
• Suriname 597
• Svalbard & Jan Mayen 47
• Sweden 46
• Switzerland 41
• Syria 963
• Taiwan 886
• Tajikistan 992
• Tanzania 255
• Thailand 66
• Timor-Leste 670
• Togo 228
• Tokelau 690
• Tonga 676
• Trinidad & Tobago 1
• Tunisia 216
• Turkey 90
• Turkmenistan 993
• Turks & Caicos Islands 1
• Tuvalu 688
• U.S. Virgin Islands 1
• Uganda 256
• Ukraine 380
• United Arab Emirates 971
• United Kingdom 44
• United States 1
• Uruguay 598
• Uzbekistan 998
• Vanuatu 678
• Vatican City 39
• Venezuela 58
• Vietnam 84
• Wallis & Futuna 681
• Western Sahara 212
• Yemen 967
• Zambia 260
• Zimbabwe 263
  
  

We are committed to creating a diverse and inclusive environment. You are invited to voluntarily indicate your gender, helping us assess the impact of our diversity efforts. All data provided will be kept strictly confidential.