Director of Inside Sales

About Meadow

To be considered please email your resume to resumes@meadowfi.com. 

Meadow is the first modern fintech platform transforming the $600 billion U.S. higher education payments industry by solving the dual complexities of the tuition payment process for students and accounts receivables for universities.

Inside Sales is the lifeblood of Meadow’s revenue growth. We’re at an exciting inflection point: our enterprise sales motion is working, demand is growing quickly, and we’re ready to scale the top-of-funnel engine that will power our next chapter. Today, our Inside Sales team is a talented group of ~10 SDRs—currently managed by our COO—who have proven what’s possible, and are ready for dedicated leadership, structure, and a high-performance cadence. The team is already successful and has the potential to do so much more.

We’re looking for a Director of Inside Sales who can take an established motion and level it up: coaching and developing SDR talent, increasing productivity across the team, leveraging tooling and partnering with Marketing to build the systems and processes that will consistently generate qualified pipeline for our sales reps.

Meadow is ready for its first true Inside Sales leader. If you’re energized by building a world-class GTM engine and creating a high-output culture that directly fuels revenue growth, we’d love to meet you.

The Role

The Director of Inside Sales will play a fundamental role in shaping Meadow's GTM engine and strategy, driving the top of the sales funnel, and building and leading a high-velocity Inside Sales team within a traditionally slow-moving industry.

You will own SDR effectiveness end-to-end: hiring, onboarding, coaching, tooling and enablement. You will partner closely with Meadow’s marketing, CX, and senior leadership to accelerate our growth with colleges and universities.

You will bring a strong, data-driven point of view on how to maximize growth through outbound and what world-class GTM looks like in 2026–and the confidence to advocate for it.

What You’ll Do

Team Leadership & Coaching

• Lead and scale our inside sales org (10 SDRs).
  
• Deliver significant hands-on coaching: daily call reviews, 1:1s, role plays, objection handling, and deal/pipeline strategy.
  
• Build a high-performance culture with clear expectations, accountability, and career pathways.

Strategy, Process & Execution

• Own inside sales playbooks: segmentation, ICP targeting, outreach strategy, talk tracks, qualification, handoffs, and follow-up loops.
  
• Establish operating rhythms (weekly campaign reviews, QA, enablement sessions, conversion rate learnings).
  
• Partner with Marketing to translate campaigns into meetings, and with AEs/founders to ensure tight conversion and feedback loops.

Data, Tooling & Continuous Improvement

• Define and manage KPI systems end-to-end: activity → conversations → meetings → qualified pipeline → closed-won contribution
  
• Build dashboards and reporting in HubSpot; identify bottlenecks and drive targeted improvements
  
• Forecast pipeline generation and capacity needs, including territory/segment planning and quota modeling
  
• Drive adoption of modern GTM tooling and workflows (sequencing, call intelligence, enrichment, scoring, QA)
  
• Pilot AI-enabled strategies (intelligent lead scoring, personalization at scale, call coaching workflows, workflow automation)
  
• Continuously test and iterate on messaging, channels, sequences, and enablement content—then standardize what works

About You

Who You Are

• A builder who has scaled sales or inside sales/SDR teams in a fast-moving environment and thrives in ambiguity.
  
• A leader who is known for hands-on coaching and improving SDR performance through consistent, high-quality feedback.
  
• A coach who is deeply data-driven: you love funnels, diagnose conversion issues, and run structured experiments to improve results.
  
• A team member who is excited about AI and sales technology—not as hype, but as practical leverage for rep productivity and quality.
  
• A strong cross-functional partner who can align marketing, sales, and CX around shared targets and tight execution.

Nice to Have

• Experience in B2B/Enterprise SaaS selling into higher education or similarly complex, relationship-driven markets.
  
• Experience scaling sales teams from early-stage to repeatable growth (hiring, management layers, enablement systems).
  
• Familiarity with HubSpot and modern SDR tooling (sequencers, dialers, conversation intelligence, enrichment).

What Success Looks Like

• A repeatable, predictable Inside Sales engine that consistently exceeds meeting, pipeline, and revenue targets.
  
• SDRs who improve week over week through hands-on coaching, call reviews, and clear development plans.
  
• A clean, measurable funnel with strong conversion, clear ownership, and fast iteration when metrics slip.
  
• Documented, tested, and continuously improving playbooks, messaging, and outbound motions across segments.
• High adoption of modern tools and AI workflows that boost productivity, improve lead quality, and eliminate low-value work.
  
• A high-performance culture with clear expectations, consistent coaching, and strong development and retention of top talent.

Compensation and Benefits

This is a full-time position reporting to the COO. Meadow wants all employees to be supported in their personal and professional development, so we take a comprehensive approach to compensation and benefits.

The OTE for this position is expected to range from $250,000 to $325,000. This range represents the low and high end for a NY-based position. Actual compensation will depend on numerous factors such as: experience, knowledge and skills, qualifications, location, and other job-related factors.

• The chance to positively impact the world while building a company around a $600B opportunity
• Earn equity in an early stage high-growth company
• Subsidized health insurance, dental coverage, vision coverage with HSA & FSA plans available
• Flexible work environment, with hybrid and fully remote roles and multiple on-sites each year
• Generous parental leave policy
• Flexible PTO along with 10 paid company holidays
• 401k retirement savings plan
• Budgeted productivity stipends 
• Working alongside an ambitious, kind, no-drama team

Meadow is proud to be an equal opportunity employer. We celebrate diversity in all its forms, and we encourage our employees to participate as their authentic selves in our work environment. We strive to build better for all, towards a more open, inclusive space. Come as you are.