Director of Sales

We're looking for a strategic and collaborative Director of Sales to help scale our go-to-market organization. In this role, you'll partner across Sales, Product, Product Marketing, Revenue Operations, Customer Experience, Recruiting, and Learning & Development to ensure our customer-facing teams have the knowledge, tools, processes, and content they need to deliver an exceptional customer experience and drive business results.

You'll serve as the connective tissue across our GTM organization—translating strategy into execution, identifying performance gaps, enabling successful product launches, and creating scalable programs that improve sales effectiveness and customer outcomes.

If you enjoy solving sales challenges, influencing cross-functional teams, and building programs that have measurable impact, we'd love to meet you.

• Design, build, and continuously improve onboarding programs to accelerate new-hire ramp time.
• Develop ongoing training programs that strengthen product knowledge, consultative selling, objection handling, and customer experience.
• Create certifications, learning paths, coaching resources, and sales enablement programs.
• Analyze sales performance trends and identify opportunities for targeted enablement initiatives.

• Analyze conversion, win/loss, and retention data to identify what's working and feed it back into training
• Review call recordings and customer interactions to surface best practices from top performers and turn them into repeatable playbooks
• Track and report on enablement-specific metrics and their downstream impact on conversion or win rate

• Partner with Product Marketing to translate positioning, messaging, and competitive insights into practical sales playbooks, talk tracks, FAQs, and customer-facing resources.
• Collaborate with Product Management to prepare customer-facing teams for product launches by developing training, enablement content, and readiness plans.
• Work closely with Marketing to ensure campaign messaging is consistently reflected throughout the customer journey.
• Partner with Revenue Operations to support CRM adoption, process improvements, sales workflows, and operational readiness.
• Collaborate with Customer Experience and Customer Success teams to improve onboarding, retention, upsell, and support experiences.
• Gather frontline feedback and communicate customer insights back to Product, Marketing, and Sales Leadership to continuously improve our GTM strategy.

• Create and refine high-converting playbooks, call scripts, objection-handling guides, and cross-sell/upsell matrices for the sales team.
• Own the organization and maintenance of sales enablement content, including playbooks, product documentation, competitive battle cards, sales presentations, and knowledge resources.
• Ensure customer-facing teams have easy access to current, accurate, and actionable enablement materials.
• Package customer proof points, case studies, and FAQs into reusable assets teams can pull from in the moment
• Develop scalable communication plans for product launches, process updates, and organizational changes.

• Own or co-own enablement tooling (e.g., CRM/helpdesk macros, content/asset libraries, call recording platforms) so teams can find the right resource in seconds, not minutes
• Partner with RevOps to keep CRM data clean and process consistent across teams

• Prior experience carrying an individual sales quota or serving in a consultative customer-facing role (Sales, Business Development, Account Management, Customer Success, Retail Leadership, or similar). You understand firsthand what it takes to build trust with customers, navigate objections, and operate in a performance-driven environment.
• 3+ years of experience in a customer-facing revenue role and/or Sales Enablement, Revenue Enablement, Sales Operations, Product Marketing, or a related GTM function.
• Experience designing and scaling enablement programs that improve onboarding, sales readiness, product adoption, or customer experience.
• Proven ability to build trusted partnerships across Sales, Product, Product Marketing, Marketing, Revenue Operations, Customer Experience, and executive leadership.
• Excellent communication and facilitation skills, with the ability to simplify complex concepts and influence audiences ranging from frontline employees to senior leaders.
• An analytical mindset with experience using performance metrics, customer feedback, and business insights to identify opportunities and measure the impact of enablement initiatives.
• A builder's mentality—you enjoy creating scalable programs, playbooks, and processes that help teams perform at their best.
• High emotional intelligence and credibility. You listen before prescribing solutions, seek to understand the realities of frontline teams, and earn trust through empathy, collaboration, and thoughtful execution.

• Experience in a direct-to-consumer, retail, consumer technology, marketplace, or high-growth environment.
• Experience supporting product launches and go-to-market initiatives across multiple customer-facing teams.
• Familiarity with CRM platforms (Salesforce, HubSpot, or similar), learning management systems, and enablement tools such as Gong, Highspot, Seismic, WorkRamp, or similar platforms.
• Experience coaching managers or facilitating leadership development programs.

After your first 60-days, you will have:

• Built scalable onboarding and ongoing enablement programs that improve sales readiness and consistency.
• Successfully enabled multiple product launches across customer-facing teams.
• Established trusted partnerships across Sales, Product, Marketing, Revenue Operations, and Customer Experience.
• Increased adoption of key sales processes, tools, and messaging.
• Demonstrated measurable improvements in ramp time, productivity, customer experience, or sales effectiveness.
• Become a strategic partner who helps connect business strategy with frontline execution.

Our customers experience our brand through every interaction with our teams. This role helps ensure those interactions are consistent, informed, and customer-centric. By connecting strategy with execution and enabling our teams to perform at their best, you'll play a critical role in helping us scale our business while delivering an outstanding customer experience.

• Amazing people with a great vision and values
• Mission-driven team culture focused on student success
• Your work directly impacts the lives and careers of students across the globe
• Health, dental, and vision insurance, base plans 100% employer paid
• Pre-tax benefits (FSA, DCFSA, HSA, Commuter)
• Flexible paid time off (PTO) and paid holidays
• 401(k) with company match