Revenue Execution Lead

Spring Health is seeking a Revenue Execution Lead to build and lead field training for our Revenue organization. Reporting to the Associate Director, Revenue Enablement, this person will design and facilitate high-impact training for Account Executives, Customer Success Managers, Account Managers, Business Development Representatives, and the revenue leaders of those teams. This is a full-time position that is fully remote. Travel may be required for company, revenue, or field-team moments.

This is a new capability within Spring Health's Revenue Enablement function. The person in this role will not simply inherit an existing program; they will define what excellent field training looks like here, build the rituals and measurement infrastructure that make it durable, and help shape the future operating model of the Revenue Enablement team. This is a full-time, fully remote position on our team. Occasional travel may be required for team or company events/meetings.

What you'll do:

• Build and deliver a practical field-training system that improves how AEs, CSMs, AMs, and BDRs learn, practice, and execute the most important motions in their roles.
• Facilitate live trainings, workshops, role-plays, manager sessions, and other field-practice moments with the presence, clarity, and credibility needed to carry a room.
• Partner with Revenue and Product Marketing leaders to diagnose execution gaps across discovery, qualification, messaging, objection handling, account strategy, expansion conversations, renewal readiness, pipeline progression, and customer value conversations.
• Translate field priorities into training programs that are simple, repeatable, and measurable, using adult-learning principles and practical reinforcement rather than one-time enablement events.
• Create formal coaching and mentorship programs that help revenue leaders and experienced ICs develop talent, reinforce key behaviors, and create stronger peer-learning loops across the organization.
• Build learning paths for different Revenue audiences, including role-specific training for AEs, CSMs, AMs, and BDRs, along with leader-facing curricula for managers field-wide.
• Use call recordings, field feedback, performance data, manager input, and learner signals to identify what is working, where execution is breaking down, and where training should be adjusted.
• Use AI thoughtfully and innovatively to increase the speed, quality, personalization, practice depth, and measurement of training while maintaining strong judgment, confidentiality, and human coaching standards.
• Build the tools, templates, facilitator guides, coaching rubrics, practice scenarios, and measurement loops that make training scalable beyond any single session.

What success looks like in this role:

• Revenue teams have a clear, repeatable field-training operating system for priority skills, role-specific practice, certification, and reinforcement.
• New hire and internal-transition ramp improves through faster time to readiness, clearer skill expectations, and stronger manager reinforcement.
• AEs, CSMs, AMs, and BDRs show observable improvement in the field behaviors targeted by training, such as discovery quality, qualification discipline, value articulation, objection handling, account planning, customer conversations, and next-step execution.
• Revenue leaders have practical coaching tools, shared language, and routines they use to reinforce training after sessions end.
• Training programs are measured with clear leading indicators, including attendance where relevant, completion, practice quality, certification outcomes, manager observation, call-quality signals, CRM or workflow adoption, and post-training behavior change.
• Training priorities are connected to business needs such as pipeline quality, conversion, deal progression, expansion readiness, renewal risk reduction, productivity, and customer-facing consistency, without overstating causation where evidence is still developing.
• The role creates durable team leverage: programs, playbooks, rubrics, AI-assisted practice flows, and coaching systems that others can operate and improve over time.
• The field experiences enablement as inclusive, practical, credible, energizing, and directly connected to the moments that determine revenue execution.

What you'll bring:

• 10+ years of experience in revenue enablement, sales training, sales leadership, customer-facing commercial roles, learning and development, or a related GTM role.
• Experience in at least one of the following: quota-carrying sales, revenue leadership, customer success/account management leadership, or field-facing enablement/training.
• Strong business acumen and the ability to connect training work to commercial execution, customer outcomes, and revenue priorities.
• Exceptional live facilitation skills, including the ability to command attention, create productive practice, manage group energy, and make complex concepts simple and actionable.
• Comfort operating in ambiguity, building from a blank page, and turning unclear field needs into focused programs with clear owners, measures, and next steps.
• Strong coaching instincts, including the ability to observe behavior, give clear feedback, and help others improve without making training feel theoretical or punitive.
• Ability to partner with senior revenue leaders and frontline managers while staying close enough to the field to understand what actually happens in calls, meetings, handoffs, and account work.
• Analytical judgment and comfort using qualitative and quantitative signals to diagnose gaps, prioritize interventions, and evaluate training effectiveness.
• Eagerness to build with AI and use it responsibly to improve role-plays and other forms of practice, along with content generation, feedback loops, manager reinforcement, and learning personalization.
• Clear, concise communication and strong project management skills, with the ability to build programs that are practical, well-run, and easy for busy field teams to adopt.

Nice to have:

• Experience in B2B, healthcare, benefits, SaaS, or complex consultative selling environments.
• Experience enabling multiple Revenue audiences, such as AEs, BDRs, Customer Success, Account Management, and frontline managers.
• Experience with sales methodologies, manager coaching systems, certification programs, onboarding/ramp programs, mentorship programs, or field coaching.
• Experience using tools such as Salesforce, Gong or other conversation-intelligence platforms, LMS tools, enablement platforms, AI assistants, or content management systems.
• Experience designing blended learning programs that combine live facilitation, asynchronous learning, peer practice, manager reinforcement, and field application.
• Experience building programs in a fast-growing or changing organization where processes are still being defined.