Mid-Market Account Executive
The Mid-Market Account Executive is responsible for winning new logos and driving expansion opportunities in the mid-market segment. Success in this role requires a hunter-first mindset, proven ability to self-source pipeline, and mastery of a structured sales process. Reps are expected to leverage AI tools for prospecting, qualification, and deal execution to maximize efficiency and conversion.
WHAT YOU’LL DO
- Own your territory and run full-cycle B2B SaaS sales from prospecting to close.
- Prospect and engage mid-level to executive buyers across industries using modern outbound techniques (email, cold calling, social outreach, referrals, and AI-assisted workflows).
- Apply a consultative, ROI-driven approach to complex sales cycles, with strong command of structured methodologies like MEDDIC, Challenger, or SPIN.
- Generate pipeline through a mix of outbound, re-engagement of closed-lost deals, and strategic account targeting.
- Collaborate cross-functionally with internal teams to deliver value and ensure a smooth customer experience.
- Contribute to a culture of grit, innovation, and teamwork.
WHO YOU ARE
- 3–5 years of SaaS sales experience with consistent quota attainment.
- Proven top-performer with history of exceeding quota.
- Disciplined in discovery, stakeholder mapping, and qualification, with mastery of structured methodologies (MEDDIC or equivalent).
- Strong outbound and pipeline generation track record.
- Comfortable leveraging AI platforms (6sense, Gong, LinkedIn automation) alongside traditional sales tools (Salesloft, ZoomInfo, LinkedIn Sales Navigator) to prioritize accounts, personalize outreach, and accelerate deal cycles.
- Polished, persuasive, and professional communicator across all levels of stakeholders.
- Bonus: Familiarity with compliance, fleet, or workforce management solutions.
Location: This role is based in our Boston office. We follow a hybrid model where team members are onsite three days per we...