Director GTM Strategy at Showpad in Boston, MA

Director GTM Strategy: Land, Expand & Ecosystem Location: US Reporting to: VP, GTM Strategy & Operations About the Role As the Director of GTM Strategy (Land, Expand & Ecosystem), you are the strategic architect of Showpad’s growth engine. You own the "Front-End" of the revenue engine, ensuring our new business, expansion, and partner motions are optimized for scale. This is a "Product Management" style leadership role where your "product" is the sales motion itself. You define the benchmarks for success and identify the AI-driven interventions needed to help the field reach them. You lead a team of analysts and strategists while personally driving the strategic direction. What You’ll Do Strategic Benchmarking: Define and set the performance benchmarks for the Land & Expand motions (e.g., Target CAC, LTV/CAC ratios, Partner-sourced pipeline %). You own the "Target" that the field is aiming for. Integrated Planning: Lead the annual and semi-annual planning cycles for the New Business, Expansion, and Partnership organizations, including capacity modeling and quota distribution. Agent Ideation & Scoping: Act as the "Field Scout" to identify high-friction manual tasks (e.g., prospecting research or partner lead routing). You define the "Job to be Done" and business logic for new AI Agents. Specialized Analysis: Own the "Last-Mile" analysis. Once the Insights team stabilizes a reporting tool, you perform deep-dives into territory health, partner attribution, and win/loss trends. UAT & Field Pilot: Lead User Acceptance Testing (UAT) for new AI tools. You run pilot groups with AEs and xDRs to ensure AI output is high-quality before global rollout. Enablement Partnership: Collaborate with the VP of Enablement on "Problem Discovery" to ensure S&O is solving the most pressing field friction points. You lead the strategic "Why" behind new tool rollouts. Ecosystem Integration: Act as the lead for the Partnerships team, defining how partners show up in territories, lead routing, and attribution models to ensure a "better together" motion. Stakeholder management: Become trusted advisor to Marketing, Sales and Finance leaders. Team Leadership: Lead, coach, and develop a team of GTM analysts and strategists. Set clear objectives, manage performance, and ensure your team is focused on the highest-impact work. You are the "player-coach"—you set the strategic direction and ensure your team has the skills and support to execute. What You Bring Experience: 8+ years in Sales/Revenue Operations, Management Consulting, or GTM Strategy. Experience in a high-growth, PE-backed SaaS environment (Vista-style) is a major plus. Proven track record of building and managing high-performing teams. Technical Literacy: Advanced proficiency in Salesforce (SFDC) and Excel/Google Sheets. Ability to translate business needs into technical requirements for an Engineering team. Strategic Thinking: Proven ability to design territory and quota models from scratch. Influence: Ability to challenge Sales and Partner leadership with data-backed insights while maintaining strong working relationships. People Leadership: Experience coaching, developing, and retaining top analytical talent. You know how to set direction and get out of the way. About Showpad At Showpad, we’re focused on empowering others to be at their best. As a global leader in AI-powered revenue effectiveness, we provide revenue teams with the platform they need to prepare sellers, engage buyers, and drive predictable revenue. Since our 2025 merger with Bigtincan, we have created the industry’s first unified platform specifically designed for complex, field-selling organizations, serving more than 2,000 customers across 50 countries. As an employer, we provide our employees with opportunities to grow, make a meaningful impact, and bring their authentic selves to work. Our culture stems from our values, which center on achieving maximum impact for our customers and fostering global collaboration, diversity, and a genuine passion for innovation. We’re a team of authentic, good-natured ass-kickers, and we’ve been recognized as a top workplace by Built In Chicago and Inc. Magazine. Why Join Us Now? Showpad is powering the next generation of field selling success through accelerated innovation, expanded global reach, and a more holistic engine to drive growth and lasting value. You’ll join a team shaping what’s next, working with smart, driven people who care deeply about making an impact (and aren’t afraid to challenge the status quo). Our Global Footprint Founded in 2011, Showpad is a global company with 500+ people (post-merger) working from offices and regional hubs around the world including Chicago, Boston, Ghent, London, Munich, Brussels, San Francisco, and Sydney. We are consistently recognized as a Leader in the Forrester Wave™ and a “Customers’ Choice” by Gartner® Peer Insights. What you can expect from Showpad We welcome every voice and are committed to building a truly inclusive environment where your differences are not just welcomed, they are celebrated. We’re building a best-in-class experience for our employees and are always identifying opportunities to encourage our team to be their authentic selves. Whether that’s paid parental leave, paid holidays (including Juneteenth and paid time off to vote), paid time off to volunteer at non-profit organizations, personal development opportunities or professional stretch assignments, you can expect Showpad to support you. We are committed to creating a diverse and inclusive organization and are proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, pregnancy, disability, age, veteran status, or other dimensions of identity. This organization participates in e-verify For more information on e-verify, click here