Regional Director of Sales

Coursedog

10h•$200,000 - $280,000•Remote

About The Position

As a Regional Director of Sales at Coursedog, you’ll drive revenue growth and expand our presence across your assigned territory, landing new institutional partners and helping shape the future of academic operations technology. You’ll own the full sales cycle — from strategic territory planning and opportunity generation to executive-level presentations and contract close — operating with autonomy and accountability in a high-growth, mission-driven environment. This role is ideal for a disciplined, execution-focused seller who thrives in complex sales cycles, enjoys building pipeline from the ground up, and is motivated by exceeding ambitious revenue targets. If you bring a strong hunter mindset, deep curiosity about customer challenges, and the ability to navigate multi-stakeholder buying processes with confidence and empathy, this is an opportunity to make a direct and measurable impact on Coursedog’s growth. This role offers a base salary, performance-driven commission, as well as additional accelerators, kickers, & other performance based incentives with total on-target earnings ranging from $200,000 to $280,000. Final compensation will be determined based on experience, skills, and market alignment.

Requirements

5+ years of experience in a full-cycle, quota-carrying SaaS sales role, with a proven track record of exceeding new business targets
Demonstrated success navigating complex enterprise sales cycles with multiple decision-makers and executive stakeholders
Deep understanding of sales methodologies such as MEDDPICC and Value Selling (certification preferred)
Experience developing and executing effective territory and account plans that translate strategy into measurable results
Strong forecasting discipline and experience maintaining CRM accuracy (Salesforce preferred)
A proactive, self-motivated working style with a strong bias toward action and ownership
Excellent communication, presentation, and facilitation skills
High emotional intelligence and the ability to approach customer conversations strategically, creatively, and empathetically
Comfort operating in a fast-paced, remote-first environment with approximately 30% travel
Familiarity with AI tools and modern sales technology to improve efficiency and effectiveness

Nice To Haves

Experience selling into Higher Education is strongly preferred

Responsibilities

Own and achieve annual quota targets within your territory, driving new logo acquisition and revenue growth
Develop and execute a strategic territory plan, including account mapping, stakeholder identification, and opportunity prioritization
Generate and maintain >4x pipeline coverage in partnership with your SDR, ensuring consistent opportunity creation and progression
Lead deep discovery conversations to uncover business challenges, define desired outcomes, and understand buying processes
Deliver highly tailored product demonstrations that align Coursedog’s platform to customer pain points and institutional priorities
Navigate complex, multi-stakeholder deal cycles, including executive-level presentations and negotiations
Own pipeline management and forecasting with a high degree of accuracy, maintaining disciplined CRM hygiene and real-time activity tracking
Apply structured sales methodologies (e.g., MEDDPICC, Value Selling) to advance opportunities and improve win rates
Proactively leverage cross-functional stakeholders (Product, Customer Success, Executive Leadership) to strengthen deals and accelerate progress
Drive industry credibility through thoughtful product evangelism and education on higher education trends
Actively solicit and incorporate feedback to continuously improve your sales approach and performance
Onsite travel travel to both customers and industry events for presentations and workshops expected 25% - 35% throughout the year.

Benefits

Healthcare, Dental & Vision
Fixed contribution model for medical, dental, and vision coverage
Company covers 65% to 99% of employee-only premiums, and 45% to 75% for employee plus dependents
Partnership with Aetna and Guardian
Access to wellness and support programs: Spring Health (mental health support), XP Health (vision benefits), Carrot Fertility (family planning support), One Medical (primary care)
Pre-tax savings through Health Savings Accounts (HSA) and Flexible Spending Accounts (FSA)
Safe Harbor 401(k) plan from day one of employment
4% employer match on total compensation for 401(k)
Unlimited Paid Time Off policy
Remote-first work environment
Equity in the company
Up to 12 weeks of fully paid parental leave