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Field Sales (Outside Sales) Representative in Boston

thoughtbot is seeking a Field Sales (Outside Sales) Representative with design or technology consulting sales experience. You will be finding, qualifying, researching, and closing consulting projects for a team of 25 software designers and developers in our Boston studio. The ideal candidate has a passion for software and customer success.

thoughtbot is a 100-person, employee-owned design and software development agency. We have been in business since 2003 and have offices in Boston, San Francisco, Austin, New York, Raleigh-Durham, and London. We offer high quality software product design and engineering services in many different technologies.

The company started in Boston in 2003, which was our sole studio until we began to expand in 2012. In Boston we have worked with organizations of all sizes to bring new products to market, or improve their existing products, including LevelUp, CarePort Health, Autodesk, ezCater,, GasBuddy, Harvard Business Review, PlacePass, the MBTA, and many more. Our Boston-based clients have billions in revenue, and employ thousands of people in Boston and beyond.

See for our core beliefs.


  • Close new projects and extensions to existing relationships.
  • Ensure the work you sell will be fulfilling to our team and aligns with thoughtbot's values.
  • Set clients up for success.
  • Develop strong long-term relationships with colleagues, clients, and partners.
  • Work closely with thoughtbot's Boston Managing Director, executive team, and sales team to optimize the team’s inbound and outbound sales processes through data-driven, results-oriented evaluation and experimentation.
  • Proactively manage project extensions, expansions, and rotations based on client and teammate needs.
  • Respond quickly to inbound requests for software product design and engineering help.
  • Assess needs and qualify fit for thoughtbot.
  • Identify key decision makers. The point of contact at our client’s organization is typically a product manager, head of design, head of engineering, head of growth, top executive, or startup founder.
  • Learn quickly about thoughtbot’s capabilities, software practices, and tools generally.


  • Experience closing design or technology consulting deals in the $50K to $2M range.
  • Ability to establish relationships with C-level clients, business and technical buyers, and other project stakeholders, providing long-term value.
  • Passion for software, customer success, continuous improvement, and quality.
  • A strong understanding of how digital product design and development projects and budgeting work.
  • Ability to redirect long feature wish lists into “jobs to be done” or “user story” thinking.
  • Discipline, attention to detail, and motivation at the prospect of growing a world-class design and software engineering consultancy.
  • A network of close contacts and the ability to leverage them into business opportunities.
  • Exceptional verbal and written communication skills.
  • Know when and how to bring thoughtbot designers or engineers into the sales process.

Extra Credit

  • Have previously founded, owned, or led a design agency or software engineering consultancy.
  • Have been an entrepreneur, designer, or programmer, delivering production software products to end users.

Our Benefits

Our goal is to provide ourselves with the best possible benefits, tools to use, and environments to work in while staying sustainable. We've shared the full details of all our benefits here.

  • Investment Time

    We consult for clients four days/week. We reserve the fifth day of each work week for continuous improvement to make ourselves, the company, and our community better by learning new tools and techniques, working on open source, blogging, creating new products, volunteering our time, and more.

  • Always Learning

    We pay 100% of expenses when you speak at conferences and 50% of the cost for attendees. We also pay 50% of all expenses for job-related training.

  • Stay Fresh

    We work a sustainable pace of 40 hours/week. We have five weeks (24 days in the UK) of vacation time per year, in addition to company holidays and sick days. For new parents, we also have at least 6 weeks paid leave in all locations, as well as the ability to take at least 6 months off.

  • Healthcare + Financial

    In the U.S. we provide competitive medical, dental, vision, and life insurance, and a comprehensive 401k plan with matching. In the UK we provide supplemental private insurance and a group personal pension scheme.

Apply for this position

thoughtbot does not discriminate on the basis of race, sex, color, religion, age, national origin, marital status, disability, veteran status, genetic information, sexual orientation, gender identity or any other reason prohibited by law in provision of employment opportunities and benefits.

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