Regional Director of Sales

The Opportunity

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.

What You’ll Do

• 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.

What You’ll Bring

• 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
• Experience selling into Higher Education is strongly preferred

Not sure if you should apply? Research shows that women and people from underrepresented backgrounds are less likely to apply unless they meet every qualification listed. At Coursedog, we’re focused on finding the best person for the role, and that person may come from a non-traditional background. We encourage you to apply even if you don’t meet every requirement — our evaluation focuses on your ability to thrive in this role and make an impact.

About Coursedog

At Coursedog, our mission is simple but ambitious: to break down barriers to student success. Founded by former college students who were frustrated by outdated academic systems, Coursedog was built to empower higher ed administrators to deliver exceptional educational experiences and make it easier for students to achieve their goals. Since then, we’ve grown into a platform trusted by institutions across the country.

Coursedog is the Intelligent Academic Operations Platform, empowering 500+ colleges and universities to better serve over 4 million students. Our platform brings together academic scheduling, curriculum and catalog management, assessment, and workflow automation — all designed to adapt to each institution’s unique needs and remove administrative roadblocks so educators can focus on helping students succeed.

We’re a remote-first, fast-growing company and a Forbes Top 500 U.S. Startup Employer, with a culture that prioritizes engagement, ownership, and impact. If you’re excited about solving meaningful problems, working with thoughtful teammates, and improving education at scale, you’ll feel right at home at Coursedog.

Working at CoursedogHealthcare, Dental & Vision

We follow a fixed contribution model to promote equity and transparency. Every employee receives the same annual dollar amount to apply toward medical, dental, and vision coverage. This approach gives you the flexibility to choose the plan that best fits your needs, whether that is a base-level option or more comprehensive coverage.

Depending on the selected coverage level, the company covers:

• Employee-only coverage: 65% to 99% of monthly premiums
• Employee plus dependents: 45% to 75% of monthly premiums

We partner with Aetna and Guardian, and offer access to best-in-class wellness and support programs, including:

• Spring Health (mental health support)
• XP Health (vision benefits)
• Carrot Fertility (family planning support)
• One Medical (primary care)

We also support pre-tax savings through Health Savings Accounts (HSA) and Flexible Spending Accounts (FSA).

Retirement Planning

To support long-term financial health, we offer a Safe Harbor 401(k) plan from day one of employment. Coursedog provides a 4% employer match on your total compensation (subject to federal limits) each pay period for employees contributing to a tax-advantaged retirement account.

Paid Time Off

We trust our employees to manage their time responsibly. That’s why we offer an unlimited Paid Time Off policy — because flexibility and balance are critical for sustained excellence and personal well-being.

Remote-First Since Inception

We were built for distributed work. Our culture emphasizes flexibility over rigidity, outcomes over hours, and transparency over gatekeeping. We are committed to being a remote-first organization indefinitely, empowering you to work where and how you thrive best.

Equity

As a valued contributor to our collective success, you’ll participate in the upside. All employees are granted equity in the company aligned to your role and tenure. Equity grants are reviewed and adjusted with promotions to reflect your evolving impact.

Paid Parental Leave

We proudly support working parents with industry-leading benefits. Employees are eligible for up to 12 weeks of fully paid leave. This benefit is available to all eligible employees, regardless of gender or family structure.