Director of Sales Enablement, Training & Go-to-Market (Boston)

About the RoleDoorDash is seeking a Director of Sales Enablement, Training & Go-to-Market to lead the design, delivery, and execution of programs that accelerate the productivity, effectiveness, and growth of our global Sales organization. You will scale enablement across our multi-faceted business model, from SaaS solutions to Ads and Marketplace partnerships, ensuring sellers are equipped with the skills, product expertise, content, and insights to win in every conversation.You will own the full enablement lifecycle: onboarding, ongoing skill development, sales methodology, manager coaching, content strategy, certification, tooling, and the operating cadence that ties them together. You will partner deeply with Sales, Product, Marketing, and Operations leaders to translate strategy into execution, making sure new capabilities are adopted quickly and consistently across all sales segments.As part of this mandate, you will also lead the deployment of AI tools, including Claude, across the Sales organization. AI is becoming core to modern selling, and you will own the strategy for embedding it into seller workflows while serving as the Sales voice in cross-functional GTM forums shaping how AI is rolled out to adjacent customer-facing teams (Customer Success, Partnerships, Marketing, and Support).By pairing operational rigor with sales coaching excellence and applied AI fluency, you will drive faster ramp times, higher productivity, stronger product adoption, and sustainable revenue growth.You’re Excited About This Opportunity Because You Will:Core Sales EnablementOwn the Onboarding Experience: Design and continuously improve new-hire onboarding for SDRs, AEs, and AMs across SMB, Mid-Market, and Enterprise segments, with clear milestones, certifications, and ramp targets that demonstrably shorten time-to-productivity.Build Continuous Learning Programs: Run a year-round curriculum of skills training, product education, segment-specific bootcamps, and sales kickoff content that keeps reps sharp and aligned with strategy.Embed a Sales Methodology: Select, customize, and operationalize a sales methodology (Challenger, MEDDIC, SPIN, or similar) across the org, with reinforcement built into pipeline reviews, deal inspection, and manager coaching.Tailor Enablement Across Business Models: Deliver differentiated playbooks and training for SaaS, Ads, and Marketplace solutions, equipping reps to position value, handle objections, run effective discovery, and cross-sell seamlessly.Own Sales Content Strategy: Build and govern a content system (pitch decks, one-pagers, case studies, battle cards, ROI tools, email templates) that is easy to find, easy to use, and continuously refreshed based on rep and customer feedback.Lead Product Adoption & Expertise: Partner with Product, Ads, and Marketing to launch new features and offerings into the field with clear positioning, training, certification, and measurement of seller readiness.Coach & Develop Sales Talent: Build a coaching culture by enabling frontline managers with frameworks, call review rituals, deal coaching playbooks, and tools to consistently raise the performance bar.Run the Enablement Operating Rhythm: Establish the cadence (intake, prioritization, launch calendar, feedback loops, post-mortems) that makes enablement predictable and trusted by Sales leadership.AI & Sales ProductivityLead AI Deployment for Sales: Own the strategy, rollout, and adoption of Claude and other AI tools across the Sales org. Build prompt libraries, AI-assisted workflows, and certification paths that turn every seller and manager into an AI power user.Elevate Sales Productivity with AI-First Workflows: Drive adoption of AI-powered workflows for prospecting, account research, call prep, proposal generation, deal coaching, and post-call follow-up. Replace manual work with intelligent automation wherever it creates leverage.Drive Measurable AI ROI: Define and track the business impact of AI in Sales, including hours saved, pipeline generated, win-rate lift, content velocity, and quality improvements, and continuously expand the use cases that move the needle.Influence GTM-Wide AI Direction: Represent Sales in cross-functional GTM AI working groups, share what’s working with CS, Marketing, Partnerships, and Support leaders, and help shape enterprise-wide standards for tooling and prompts, without owning execution outside Sales.Support Responsible AI Use: Partner with Legal, Security, and IT to apply DoorDash’s AI usage guidelines, data handling policies, and quality controls within Sales, and feed Sales learnings back into enterprise policy.Leadership & ImpactOwn Business Impact Metrics: Define and track KPIs including ramp time, quota attainment, seller productivity, content utilization, certification rates, and incremental revenue growth attributable to enablement programs.Strengthen XFN Partnerships: Act as the connective tissue between Sales and cross-functional stakeholders (Product, Ops, Marketing, IT, Legal), ensuring alignment on GTM priorities, seamless rollouts of new initiatives, and continuous feedback loops to Product and Ops.Lead and Inspire: Manage and develop a high-performing global team of enablement managers, trainers, instructional designers, coaches, and GTM program leads.We’re Excited About You Because:12+ years of experience in Sales Enablement, Training, or Sales Leadership in high-growth SaaS, Ads, or Marketplace companies, with at least 5+ years leading enablement teams.Proven track record of designing onboarding and continuous-learning programs that measurably reduced ramp time and increased quota attainment at scale.Deep knowledge of modern sales methodologies (Challenger, MEDDIC, SPIN) and demonstrated experience embedding them across a multi-segment sales org.Strong content strategy chops, including governance, taxonomy, sales content tooling, and measurement of content effectiveness.Skilled at designing and leading manager coaching frameworks, call review programs, and deal inspection rituals that improve win rates and deal velocity.Experience tailoring enablement to multiple business models (e.g., SaaS subscriptions, Ads, Marketplace) and multiple segments (SMB, Mid-Market, Enterprise).Applied AI deployment experience: You have personally rolled out LLM-based tools (Claude, ChatGPT Enterprise, Copilot, or similar) to a sales org and can speak credibly to prompt design, workflow integration, change management, adoption metrics, and measurable outcomes.AI fluency in practice, not just theory: Comfortable with prompt engineering, evaluating model outputs, designing human-in-the-loop workflows, and integrating AI with CRM, enablement, and conversation intelligence platforms.Experienced in building cross-functional partnerships with Product, Marketing, and Operations, and comfortable representing Sales in broader GTM forums.Strategic GTM thinker able to translate complex product roadmaps into clear, actionable sales motions.Exceptional leadership and team-building skills with a global mindset.Excellent communication, facilitation, and executive presence, with a data-driven approach.Familiarity with enablement platforms (Highspot, Seismic, Mindtickle), conversation intelligence (Gong, Chorus), LMS tools, CRM systems (Salesforce preferred), and enterprise AI platforms (Anthropic Claude, OpenAI, Google).CompensationThe successful candidate’s starting pay will fall within the pay range listed below and is determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Base salary is localized according to an employee’s work location. Ranges are market-dependent and may be modified in the future.In addition to base salary, the compensation for this role includes opportunities for equity grants. Talk to your recruiter for more information.DoorDash cares about you and your overall well-being. That’s why we offer a comprehensive benefits package to all regular employees, which includes a 401(k) plan with employer matching, 16 weeks of paid parental leave, wellness benefits, commuter benefits match, paid time off and paid sick leave in compliance with applicable laws (e.g. Colorado Healthy Families and Workplaces Act). DoorDash also offers medical, dental, and vision benefits, 11 paid holidays, disability and basic life insurance, family-forming assistance, and a mental health program, among others.To learn more about our benefits, visit our careers page here.See below for paid time off details:For salaried roles: flexible paid time off/vacation, plus 80 hours of paid sick time per year.For hourly roles: vacation accrued at about 1 hour for every 25.97 hours worked (e.g. about 6.7 hours/month if working 40 hours/week; about 3.4 hours/month if working 20 hours/week), and paid sick time accrued at 1 hour for every 30 hours worked (e.g. about 5.8 hours/month if working 40 hours/week; about 2.9 hours/month if working 20 hours/week).The national base pay range for this position within the United States, including Illinois and Colorado.$187,000—$275,000 USDAbout DoorDashAt DoorDash, our mission to empower local economies shapes how our team members move quickly, learn, and reiterate in order to make impactful decisions that display empathy for our range of users—from Dashers to merchant partners to consumers. We are a technology and logistics company that started by enabling door-to-door delivery, and we are looking for team members who can help us go from a company that is known as the place you order food to a company that people turn to for any and all goods.DoorDash is growing rapidly and changing constantly, which gives our team members the opportunity to share their unique perspectives, solve new challenges, and own their careers. We're committed to supporting employees’ happiness, healthiness, and overall well-being by providing comprehensive benefits and perks includin