Director of Enterprise Sales

Lead our enterprise sales organization as Director of Enterprise Sales, driving FastStartup's expansion into Fortune 500 accounts and establishing us as the premier AI implementation partner for the world's largest enterprises. This executive-level role requires someone who has successfully built and scaled enterprise sales teams from $50M in ARR, with deep experience navigating the complex politics, procurement processes, and extended sales cycles characteristic of global 2000 accounts. You'll own relationships with C-suite executives at our most strategic accounts (think: Fortune 100 financial services, pharmaceutical companies, and tech giants), orchestrate $5M-$20M+ deals involving multiple business units and geographies, and build the playbooks, processes, and team structure needed to make enterprise sales a repeatable growth engine. Beyond closing deals yourself, you'll recruit, develop, and lead a team of enterprise AEs and solution engineers, establishing FastStartup's enterprise sales culture and methodology. This role reports directly to the CEO and will evolve into VP of Sales as the company scales. Responsibilities Own and drive the entire enterprise sales strategy, including account selection, outreach sequences, sales methodology, proposal frameworks, and negotiation tactics Personally manage relationships with 5-10 strategic enterprise accounts, serving as the primary executive sponsor and ultimate escalation point Lead complex, multi-million dollar sales cycles involving extensive discovery, solution design, proof-of-concept projects, executive presentations, and legal negotiations Build and scale the enterprise sales team from 2-3 AEs to 10+ over 18-24 months, including hiring, onboarding, training, and performance management Develop enterprise sales playbooks covering everything from account research and executive outreach to competitive positioning and objection handling Establish key performance indicators, pipeline metrics, and forecasting models that provide visibility into enterprise sales performance Collaborate with marketing, product, and delivery teams to ensure alignment on enterprise customer needs, competitive positioning, and solution development Represent FastStartup in high-stakes client meetings, contract negotiations, and escalations requiring senior leadership involvement Build strategic partnerships with system integrators, technology vendors, and consulting firms to expand enterprise reach and co-selling capabilities Provide regular updates to CEO and board on enterprise sales performance, market trends, and strategic opportunities Requirements 12+ years of enterprise B2B sales experience with at least 5 years in senior leadership roles (Director, VP, or Head of Sales) Proven track record of scaling enterprise sales organizations from early stage ($5-10M ARR) to growth stage ($50M+ ARR) Deep expertise selling complex professional services or enterprise software to Fortune 500 companies with deal sizes ranging from $2M to $20M+ Extensive network of relationships with C-level executives at target enterprise accounts Experience building and leading high-performing sales teams including hiring A-players, designing compensation plans, and coaching for success Strategic thinker with ability to develop go-to-market strategies, identify white space opportunities, and position against entrenched competitors Strong operational discipline with experience implementing CRM systems, sales processes, and forecasting methodologies Exceptional communication and executive presence—comfortable presenting to boards of directors and C-suite executives Understanding of AI/ML technologies and their business applications preferred but not required MBA from top-tier institution preferred; Bachelor's degree required #J-18808-Ljbffr FastStartup