Director of Product, DESSA

About Riverside Insights 

At Riverside Insights, we believe no student should go overlooked or underserved. Our mission is to expand opportunity for all learners by building the world’s highest-performing, double bottom line education company. We create assessment and data solutions that help every student be seen, understood, and supported. 

About DESSA 

DESSA is a leading K–12 mental health, behavior, and social-emotional learning solution that is evolving into the life skills and whole learner space as the category matures. Districts rely on DESSA to identify needs, personalize supports, and measure student growth across resilience, collaboration, and other essential competencies for life and learning. 

The next chapter is significant: new markets, new products, new positioning, and new levels of adoption. We are searching for an entrepreneurial product leader who can help us unlock that next chapter. 

If you are energized by building what is next and passionate about helping every student thrive, we would love to meet you. 

The Opportunity 

We’re hiring a Director of Product, DESSA with the mindset of a true Product GM - someone who blends strong product intuition, commercial acumen, and a deep understanding of early childhood education. In this role, you’ll own the end-to-end strategy, roadmap, pricing, and execution for your product line, collaborating across Product, Engineering, Sales, Marketing, and Research to deliver measurable outcomes for teachers and learners.

This is a high-visibility, high-impact leadership role - a key driver of Riverside’s next chapter of growth and innovation. 

What You’ll Do

• Define and own DESSA’s multi-year growth strategy and roadmap
• Expand TAM, adoption, and impact across states, districts, and classrooms
• Refine pricing, packaging, and positioning that maximize value 
• Translate strategy into clear product requirements for engineering
• Partner with engineering to ensure predictable delivery and technical quality 
• Align with Sales and Marketing on launch, messaging, and adoption plays
• Embed educator and district insight into product decisions 
• Pilot, measure, and scale what works
• Build partnerships that unlock new channels and influence 
• Serve as a credible external voice in all communities
• Track metrics that drive sustainable business and student impact 

Success Looks Like 

In three years, you will have:

• Doubled DESSA’s revenue through a clear growth strategy and successful product evolution
• Positioned DESSA as the leading life skills solution that resonates nationally
• Delivered roadmap initiatives that improve engagement, fidelity, and ROI for districts
• Created a repeatable GTM motion that scales adoption and expansion
• Built real excitement and advocacy among educators, district leaders, and influencers 

Who You Are 

A successful candidate will excel in the following areas: 

Strategic and Commercial Leader

• Knows how to expand reach, usage, revenue, and brand
• Makes savvy tradeoffs that drive both short- and long-term growth
• Partners closely with Sales and Marketing to ensure GTM effectiveness and adoption 

Product and Market Expert

• Experience in K–12, assessment, SEL/MTSS, or related domains strongly preferred
• Comfort navigating the evolving SEL to life skills positioning 

Cross Functional Driver

• Skilled at influencing without authority and managing a matrix to outcomes
• Thrives in ambiguity; creates order, movement, and accountability 

SaaS Builder

• Adept at turning customer insights into scalable, technically feasible solutions
• Skilled in prioritization, technical tradeoffs, and sequencing to accelerate delivery 

Market Facing Evangelist

• Confident being the face of DESSA at conferences, with districts, and in the press
• Understands the political nuances across regions and adapts messaging appropriately 

Entrepreneurial Owner

• Scrappy, urgent, resourceful; willing to build the pitch, make the call, test the idea
• Strong judgment under pressure; hungry to win 

What You’ll Bring:

• Builder energy: you move quickly, remove barriers, and create clarity 
• Strategic discipline: you focus on the levers that drive adoption and market expansion
• Teacher-centric empathy: you understand classroom workflows and how teachers think, purchase, and share 
• Owner mindset: you are accountable for measurable business outcomes 

• Medical, Dental, and Vision plans
• Company paid basic life and AD&D insurance
• Company paid long-term disability 
• Paid Parental Leave
• Supplemental life insurance options  
• Company paid Employee Assistance Program (EAP) 
• Retirement plan with discretionary company matching  
• Flexible Spending Account (FSA) and Health Savings Account (HSA) options 
• Premium subscription to Calm for employee and dependents 
• 33 days of company paid time off (PTO, Holidays, Wellness Days)   
• Quarterly Focus Days
• Flexible work arrangements
• Tuition Reimbursement Program
• Company orientation and 30/60/90 Day Onboarding 

Compensation: A reasonable estimate of the OTE range for this position is $170,000 - $220,000 USD (base plus bonus). This compensation range is specific to the United States, and it incorporates many factors including but not limited to an applicant's skills and prior relevant experience and training; licensures, degrees, and certifications; internal pay ranges; and market data/range parameters.