Founding Sales Development Representative

Clarasight; Boston (MA); On-site; USD 60,000 - 80,000; Full time

Job summary

Clarasight is seeking a proactive SDR to join our team and scale outbound motion. You will work directly with the founders to build a scalable pipeline, using MEDDPICC training and AI-powered research to target senior decision-makers at enterprise accounts.

This role offers fast promotion paths to Enterprise Account Executive for top performers. You’ll collaborate with Sales and Marketing to refine targeting, messaging, and sequencing while learning modern outbound best practices in a startup

Qualifications

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

Responsibilities

• Identify and engage senior decision-makers at large enterprise accounts via multi-channel outreach (phone, email, LinkedIn).
• Develop strategic selling insights linking travel with cost and risk to drive executive conversations.
• Collaborate with Sales and Marketing to refine targeting, messaging, and sequencing.

Skills

Enterprise sales exposure

B2B GTM familiarity

AI-assisted outreach

Ability to learn MEDDPICC

Job description

About Us

Clarasight is 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 us to turn travel spend into a strategic advantage. We are growing fast, landing marquee logos, and building the GTM engine that will define the next chapter.

About You

You are genuinely curious about how businesses work — how companies operate, how executives think, and how travel fits into that picture. You communicate with clarity and confidence, equally at home on the phone with a CFO or writing a cold email. You are resilient, able to hear no all day, stay positive, and come back sharper tomorrow. You think in systems, not one-offs: you don't just want to book one meeting, you want to figure out how to book a hundred. You treat AI tools as a default, not a novelty.

About the Role

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.

Key Responsibilities

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

You'll Be a Great Fit If You…

• 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

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.