Director of Mid-Market Sales

HockeyStack is building the agent infrastructure for enterprise revenue. We spent five years building the only data architecture that preserves causality across the full revenue stack — every interaction, every signal, in sequence. On top of that foundation, we built Nex-lm, a purpose-built AI engine that compiles natural language into deterministic agent workflows. The result is a platform that can extract the revenue blueprint from a company's data, encode it into repeatable automations, and execute it across sales, marketing, and customer success — consistently, at scale. We are not building a dashboard tool with an AI feature. We are building the operating layer that replaces the human bottleneck in enterprise revenue organizations. This is a category being defined right now, and we intend to own it. We have raised $50M+ from Bessemer Venture Partners, General Catalyst, Y Combinator, and others. We move fast and we hire people who want to win. Since launching late 2023, we have grown to 8-figures in ARR, process over 60 TB of revenue data monthly, and we are working with some of the largest B2B companies in the world like Microsoft, Harvey, New Relic, Collibra, etc. 🚀 YOUR MISSION As Director of Mid-Market Sales at HockeyStack, you will own the commercial success of our Mid-Market segment. This is a true player-coach leadership role where you’ll build, coach, and scale a high-performing team of Account Executives while delivering predictable, repeatable revenue growth. You’ll operate at the intersection of data, product, and go-to-market execution, translating HockeyStack’s value into clear business outcomes for mid-market customers. Your leadership will directly shape our revenue engine, sales culture, and how we win this segment as we scale. This role is ideal for a sales leader who wants real ownership, thrives in fast-moving environments, and stays close to the work. 🔧 WHAT YOU’LL DO Own Mid-Market revenue - Be accountable for annual, quarterly, and monthly revenue targets - Drive consistent attainment through pipeline generation, deal inspection, and closing rigor Lead and develop a high-performing AE team - Recruit, hire, onboard, coach, and retain top-tier Mid-Market Account Executives - Provide ongoing deal strategy, 1:1 coaching, and performance management Run a best-in-class sales process - Enforce consistent execution across prospecting, qualification, discovery, negotiation, and close - Maintain forecast accuracy, pipeline hygiene, and commit discipline Be hands-on with customers and deals - Join strategic sales calls, executive conversations, and complex negotiations - Coach the team on articulating ROI, business impact, and value to senior decision-makers Partner cross-functionally - Work closely with Solutions Consulting on solution positioning - Collaborate with Marketing, RevOps, Product, and Customer Success to improve GTM execution Build for scale - Design and refine territory plans, segment strategy, and account coverage - Codify sales playbooks, enablement, and repeatable motions as the team grows - Identify and remove gaps in process, tooling, or execution 🧬 WHAT WE’RE LOOKING FOR Experience & Background - 7+ years of progressive B2B SaaS sales experience - 3–5+ years leading a team of full-cycle Account Executives in Mid-Market - Proven experience selling complex cloud software - Experience across both high-growth startups and established SaaS environments - Track record selling ACVs of ~$25k–$250k with deal cycles under ~6 months Commercial & Leadership Strength - Consistent record of meeting or exceeding team revenue targets - Strong command of pipeline strategy, forecasting, and deal inspection - Ability to coach complex, multi-stakeholder executive sales cycles - Proven ability to recruit, develop, and retain top sales talent - Experience working cross-functionally with GTM teams Mindset & Attributes - Hands-on, proactive, and highly autonomous—leads by example - Strong business and financial...