Senior Manager, B2B Sales

📋 Description

• • Own the entire revenue engine. As Senior Manager, B2B Sales you will architect, run, and continuously optimize the end-to-end sales motion that turns Clasp’s mission into predictable, scalable revenue. You are the connective tissue between product-market fit and aggressive growth targets, ensuring every rep, campaign, and customer conversation ladders up to our north-star goal of democratizing access to education and career mobility.
• • Coach, mentor, and elevate a high-performing team. You will directly manage quota-carrying Account Executives and SDRs, running weekly 1:1s, call reviews, and deal clinics that sharpen skills in discovery, objection handling, negotiation, and closing. Your coaching philosophy balances empathy with radical candor—celebrating wins publicly, dissecting losses candidly, and turning every interaction into a learning moment that compounds rep performance.
• • Build and institutionalize a repeatable sales process. From lead scoring and MQL-to-SQL criteria to MEDDPICC qualification, mutual action plans, and executive sponsor playbooks, you will document, train, and enforce best practices that reduce ramp time for new hires and compress sales cycles for complex enterprise deals. You own the CRM hygiene gospel—HubSpot is your canvas—ensuring data integrity that powers forecasting accuracy within 5%.
• • Partner obsessively with Marketing to create a unified revenue narrative. You will sit shoulder-to-shoulder with demand-gen, content, and product marketing to align ICP definitions, campaign messaging, and ABM plays that fill the top of funnel with high-intent prospects. Joint OKRs include pipeline coverage ratios, stage-2 conversion rates, and CAC payback periods, all tracked in a shared RevOps dashboard you help design.
• • Run disciplined pipeline and forecast reviews. Every Monday you will lead a 60-minute forecast call where reps present deal strategy, next steps, and risk mitigation plans. You apply a data-driven lens—win-rate by segment, multi-threading depth, competitive threats—to surface red flags early and reallocate resources to the highest-impact opportunities. Your forecast is the single source of truth the CEO and board rely on.
• • Serve as executive sponsor and strategic closer for marquee deals. When a Fortune 500 CHRO or benefits leader needs to hear from a peer-level voice, you step in. You will quarterback multi-stakeholder presentations, ROI models, and legal negotiations, leveraging your storytelling prowess to translate Clasp’s social impact into hard-dollar business value—reducing turnover, boosting DEI metrics, and unlocking tuition assistance budgets.
• • Translate customer insights into product and process improvements. By debriefing closed-won and closed-lost deals with Partner Success, you will feed real-world pain points back to Product and Engineering, influencing roadmap priorities such as new repayment integrations or analytics dashboards. Your voice ensures sales is not just a revenue function but a strategic sensor for market needs.
• • Evangelize Clasp at industry conferences, SHRM chapters, and fintech meetups. You will represent the company on panels, podcasts, and webinars, positioning Clasp as the definitive thought leader in education benefits and workforce development. Your public-speaking magnetism generates inbound pipeline and reinforces our Forbes Fintech 50 brand equity.
• • Scale the team for hyper-growth. Over the next 18 months you will design hiring profiles, interview loops, and onboarding bootcamps that double the sales organization while maintaining culture and performance standards. You will introduce comp plan iterations, SPIFFs, and career-pathing frameworks that attract top-tier talent and reduce regrettable attrition to <10%.
• • Champion a culture of experimentation and continuous improvement. Whether piloting a PLG motion, testing new pricing tiers, or leveraging AI-driven lead scoring, you foster a “win or learn” mindset where calculated risks are celebrated and failures are mined for insights. Your leadership ensures Clasp remains agile as we expand into new verticals and geographies.