Founding Sales Development Representative

Who you are

• You are genuinely curious about business: how companies work, how executives think, and how travel fits into that picture
• You communicate with clarity and confidence, whether on the phone with a CFO or writing a cold email
• You are resilient: you can hear no all day, stay positive, and come back sharper tomorrow
• You think in systems: you don't just want to book one meeting, you want to figure out how to book a hundred
• You are comfortable with AI tools and expect to use them as a default, not a novelty
• 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

What the job involves

• This is not a traditional SDR role. You will be the first SDR at Clarasight, working directly with our co-founders to scale the outbound motion. You will be trained on MEDDPICC from day one, and top performers have a clear path to enterprise Account Executive within 12 months. No politics. No waiting list
• Outbound & Pipeline Generation
• Identify and engage senior decision-makers (Finance, Procurement, HR, Operations) at large enterprise accounts through cold outreach across phone, email, LinkedIn, and events
• Multi-thread into accounts and expand coverage within existing opportunities
• Strategic Selling
• Develop exec-level insight into how travel intersects with cost, risk, and business performance — driving strategic conversations, not just booking meetings
• Building the Motion
• Help define what modern outbound looks like by testing approaches across channels, creating repeatable frameworks, and reporting back what is landing and what is not
• Leverage AI tools by default to research accounts, personalize outreach at scale, and sharpen targeting
• Cross-Functional Collaboration
• Work closely with Sales and Marketing to refine targeting, messaging, and sequencing

Benefits

• Fully remote: We are a remote-first team with an inclusive culture that enables freedom and flexibility
• Unlimited PTO with mandatory minimums: We believe rest, rejuvenation and time away from work is critical. Our PTO policy fully reflects this
• Education and Sustainability budgets: Each teammate receives an annual budget to invest in learnings and personal sustainability
• Industry leading insurance plans: We have robust medical, dental and vision plans and cover 100% of individual premiums
• Equity incentive plan: Every full-time employee receives stock options in the company. We are all owners in the business
• 401k: We offer 401k plans to every full-time employee, and enable sustainable investments funds as well