Fast Facts

Join Riverside Insights as the Director of Product for DESSA, where you'll lead the growth strategy for a K–12 mental health and social-emotional learning solution, transforming the way educational needs are identified and supported.

Responsibilities: Define and execute DESSA's growth strategy, refine product positioning, collaborate with cross-functional teams, and build educator partnerships to drive measurable impacts on student learning.

Skills: Strong product management skills, commercial acumen, familiarity with K–12 education, and experience in social-emotional and behavioral learning solutions are essential.

Qualifications: Candidates should possess a background in K–12 education or related fields, with experience in assessments and social-emotional learning preferred.

Location: This position is based in the USA and may offer remote work options.

Compensation: $170000 - $220000 / Annually

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.

Mental Health Solutions EdTech Jobs

Director of Product, DESSA