Founding Sales Development Representative

Location: Boston; London; New York City

Employment Type: Full time

Location Type: Hybrid

Department: Sales

About Us: Join us in building the leading AI-Powered Mission Control for Corporate Travel. Some of the world's most recognizable companies, representing over $5B in managed travel spend, rely on Clarasight to turn travel spend into a strategic advantage.

About You: You want to be a founder. But you are smart enough to know that founders who cannot sell do not last. You spent time in consulting, investment banking, private equity, or came up in a role where the quality of your thinking was the product. You know how to build a point of view, earn credibility in a room full of senior executives, and turn a spreadsheet into a boardroom conversation. Now you want to build something — and you are looking for the right on-ramp. This is not a traditional SDR role. We are not looking for someone to blast sequences and hit dial counts. We are looking for someone who understands that the best pipeline comes from insight, not volume. Someone who is humble enough to pick up the phone all day and resilient enough to stay positive when the answer is no. Someone who sees AI as a tool to do things better, not just faster. If that is you, read on.

About the Role: Clarasight is hiring a Founding SDR (GTM Builder) to help us build the pipeline engine that will define how we grow. You will work directly with Phil, our co-founder, and our sales team. You will open doors at the senior executive level inside large enterprise organizations. You will develop deep insight into how travel intersects with business priorities — and give executives a reason to take the meeting. There is no playbook yet. You will help write it.

Key Responsibilities:

• Build and qualify pipeline
• Identify and engage senior decision makers across Finance, Procurement, HR, and Operations at large enterprise accounts
• Multi-thread into new accounts and expand coverage within existing opportunities
• Develop exec-level insight into how travel intersects with cost, risk, and business performance — and use that to drive conversations, not just book meetings
• Partner closely with Sales and Marketing to refine targeting, messaging, and sequencing
• Build the GTM model
• Help define what modern outbound looks like when you build it from scratch
• Develop and test approaches across phone, email, LinkedIn, and events
• Create repeatable frameworks that improve conversion without sacrificing quality
• Bring back what you're hearing — what's landing, what's not — to shape the product and the pitch

What success looks like in 6–12 months:

• Booking 12–15 qualified meetings per month
• Meetings held with the right people, with show rate above 80% and AEs accepting them as qualified
• Multi-threaded across target accounts, not reliant on a single contact
• A documented playbook of what works: messaging, channels, personas, entry points
• A clear point of view on what great outbound looks like — and active work building it

You’ll Be a Great Fit If You…

• Have 2–4 years of experience in consulting, investment banking, private equity, or a role where the quality of your thinking was the product, and are ready to do something different
• Are genuinely curious about business — how companies work, how executives think, and how travel fits into that picture
• Are resilient. You can hear no all day, stay positive, and come back sharper tomorrow
• Communicate with clarity and confidence whether you’re on the phone with a CFO or writing a cold email
• Think in systems. You don’t want to book one meeting — you want to figure out how to book a hundred
• Are comfortable with AI tools and expect to use them as a default, not a novelty
• Love travel. Not as a perk — as a genuine interest in an industry that is more complex and more interesting than most people realize

Nice to Haves:

• Exposure to enterprise software sales or B2B GTM
• Familiarity with the corporate travel ecosystem (TMC, OBT, expense, card)
• Experience building something, even outside of work
• Experience working alongside AI systems and applying human judgment to automated outputs

Diverse Perspectives: We know that innovation thrives on teams where diverse points of view come together to solve hard problems in ways that are just now possible. As such, we explicitly seek people that bring diverse life experiences, diverse educational backgrounds, diverse cultures, and diverse work experiences. Please be prepared to share with us how your perspective will bring something unique and valuable to our team.