Founding Sales Development Representative

Clarasight • Boston, MA

3d

About The Position

Clarasight is hiring a Founding SDR (GTM Builder) to help build the pipeline engine that will define how the company grows. This role is not a traditional SDR position focused on high-volume outreach. Instead, it seeks an individual who understands that the best pipeline comes from insight, not volume. The ideal candidate will be humble enough to make calls all day, resilient enough to stay positive when facing rejection, and see AI as a tool for improvement. The SDR will work directly with the co-founder and sales team, opening doors at the senior executive level in large enterprise organizations. They will develop a deep understanding of how travel intersects with business priorities to give executives a reason to take meetings. This role involves helping to write the playbook for how the company grows, as there is no existing one.

Success in this role within 6-12 months involves booking 12-15 qualified meetings per month with the right people, achieving an 80% show rate, and having those meetings accepted by Account Executives as qualified. The SDR should become multi-threaded across target accounts, not reliant on a single contact. They will also contribute to a documented playbook of effective messaging, channels, personas, and entry points, and develop a clear point of view on what constitutes great outbound sales.

The company values diverse perspectives and explicitly seeks individuals with diverse life experiences, educational backgrounds, cultures, and work experiences, believing that innovation thrives when these diverse viewpoints converge to solve complex problems.

Requirements

• 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
• Genuinely curious about business — how companies work, how executives think, and how travel fits into that picture
• 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 just want to book one meeting — you want to figure out how to book a hundred
• 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

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
• 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 This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed