Remote Pilot Operator Jobs in Dedham, MA (NOW HIRING)

We Impact Lives Through Purpose-Driven Work in A People First Culture
Ascend Learning, a leading healthcare and learning technology company, is the connection between a powerful portfolio of brands serving students, educators, and employers with outcomes-based, data-driven solutions across the lifecycle of learning. From testing to certification, Ascend Learning products are used by physicians, emergency medical professionals, nurses, allied health professionals, certified personal trainers, financial advisors, skilled trades professionals and insurance brokers.
Headquartered in Burlington, MA, with additional office locations and hybrid and remote workers in cities across the U.S., Ascend Learning was recognized by Newsweek and Plant-A Insights Group as one of America's 2025 Greatest Workplaces as well as America's Best Places to work for Mental Well-Being for 2025.
We're always looking for talented, passionate professionals to join us in our mission to help change lives. If this sounds like an environment where you'd thrive, read on to learn more.
WHAT YOU'LL DO
We are hiring a Senior Director of Product Management to lead the strategy, team, and outcomes for a portfolio of Allied Health product lines. You'll operate at the intersection of healthcare education, technology, commercial strategy, and people leadership. You're as comfortable negotiating a contract redline with Legal as you are running a discovery sprint or presenting a growth thesis to the executive team.
The best candidate for this role will have sharp product instincts earned as a practitioner, a proven ability to develop that same instinct in others, and a demonstrated record of identifying new product bets and developing them into measurable commercial wins. You've scaled a multi-product portfolio at a growth-stage company, and you know how to bring that same entrepreneurial edge into an organization built for scale without losing the speed or conviction that got you here.
You multiply your impact through the product managers you develop, not just through the decisions you make yourself. When you succeed in this role, you'll make a measurable impact on allied health workforce readiness, student completion rates, portfolio revenue through the strength of the team and products you build.
We operate with high transparency, high ownership, and a strong preference for written communication and asynchronous alignment. We are actively building a more product-led culture and want product leaders who will help shape - not just adapt to - that culture.
WHERE YOU'LL WORK
This position will have the flexibility to work remotely within the United States.
WHAT YOU'LL OWN
Strategy. Product vision, strategy, and portfolio roadmap.

• Define and own the multi-year product vision and annual strategy across the Allied Health product lines grounded in market dynamics, customer insight, and Ascend's strategic priorities.
• Identify and prioritize new growth vectors for the portfolio, new products, adjacent markets, partnerships, or business models.
• Treat pricing, packaging, and positioning as strategic levers, not fixed constraints to unlock adoption, retention, or revenue growth.
• Set a compelling narrative for the portfolio that makes the "why" clear and inspires aligned action across teams.
• Support unified portfolio-level prioritization. Make hard trade-off calls across multiple product areas, with clear reasoning that's visible to your team and to leadership.
• Build a repeatable discipline for testing new growth bets by piloting, measuring, and scaling ideas. Balance near-term commercial pressure with platform investment and long-term strategic bets, and defend that balance credibly in front of senior stakeholders.

Team Leadership. Build and develop the product management bench.

• Hire, coach, and manage teams across multiple brands including product managers, content developers and product engineers holding a high bar for both product craft and commercial judgment. Create a bench strong enough that the product line thrives even when you're not in the room.
• Manage / Build the operating rhythm, standards, and review cadence that make your team better with clear expectations for discovery rigor, requirements quality, and outcome ownership.

Commercial Outcomes. New product launches and measurable business impact.

• Own a track record of taking new products from concept to launch to durable commercial results.
• Define the commercial thesis for each major bet: what impact it should have on revenue, retention, or expansion, and hold the team accountable to it post-launch.
• Partner with Finance to build and defend business cases, pricing models, and investment trade-offs for the portfolio.
• Drive measurable growth and total addressable market expansion to achieve organizational strategies.

Cross-Functional Partnership. Partner with Engineering, GTM, Finance, and Legal

• Engineering: Partner as a peer on sequencing, technical investment, and architectural trade-offs - not just as a requirements provider.
• GTM: Shape positioning, packaging, pricing, and launch strategy; personally represent the product line in key customer and sales conversations.
• Finance: Own the commercial case for product bets, including margin, cost-to-serve, and revenue impact, before and after launch.
• Legal: Anticipate the contracting, data, security, and compliance terms that determine whether a product actually closes and renews with institutional customers.

AI-Enabled Product Development. Practical, business-driven use of AI.

• Bring a track record of using AI to solve real business or customer problems and to create commercial value - not experimentation for its own sake.
• Have sufficient technical fluency in AI/ML approaches (e.g., recommendation systems, adaptive content, embeddings) to partner credibly with engineering and data science on feasibility, design tradeoffs, and build-vs-buy decisions
• Identify where AI genuinely improves the product's value proposition or unit economics, and make the call on where it doesn't (yet) justify the investment.
• Ensure AI-enabled features meet the data privacy, accessibility, and content-quality standards required for an education audience, treating responsible AI use as a product requirement rather than an afterthought. Set the bar for your team's use of AI in product development, discovery, and decision-making, grounded in evidence of business impact.

Outcomes & Measurement. Portfolio-level performance.

• Define leading and lagging success metrics for portfolio initiatives, and ensure your team instruments products to measure them.
• Own the performance of the growth portfolio: retention, engagement, activation, NPS, and revenue contribution. Report on it with clear, data-grounded storytelling to senior leadership..Define and measure efficacy metrics that demonstrate how the portfolio measurably improves customer and learner outcomes - not just usage of a feature, but evidence it helped the people using it succeed.

WHAT WE'RE LOOKING FOR
We care about what you've done and how you think - not just what's on your resume.

• 10+ years of progressively responsible relevant experience, with demonstrated commercial impact in product management or software engineering within product-led technology companies. You should be able to show the quantifiable impact your product work has had on the P&L of a business or business unit.
• 5+ years managing teams of product managers in a product-led technology company, with a track record of developing PMs into stronger, more independent operators.
• A track record of driving the launch of new products with measurable commercial impact - you can point to specific launches and the revenue, retention, or expansion results that followed.
• Demonstrated ability to partner equally well with Engineering, GTM, Finance, and Legal to develop products that are both commercially viable and genuinely solve customer pain points - and that hold up through commercial contracting and procurement with customers.
• Significant, specific examples of using AI to solve practical business problems and build commercial products - you can speak concretely to the business value created, not just the technology used.
• Sharp product sense, sharpened further by having taught it to others. You have a well-honed instinct for what customers need and can recognize (and correct) when a product manager's instinct is off.
• Deep technical acumen. You can credibly assess technical trade-offs, sequencing, and architecture decisions in partnership with Engineering leadership, even though you don't need to write code yourself.
• Quantitative rigor. You're fluent in both technical and business data, comfortable defining metrics, running experiments, and reasoning from evidence at the portfolio level. Experience with analytics tools (e.g., Amplitude, Mixpanel, Tableau, SQL) is a plus.
• Exceptional written and verbal communication - able to write a sharp strategy memo, run a tight portfolio review, and present to a C-suite or Board audience with equal effectiveness.
• Comfort with ambiguity and organizational complexity - you can operate without a full playbook, make good decisions under uncertainty, and course-correct quickly when you're wrong.

Preferred Experience:

• Experience in education technology, healthcare, or a regulated industry where deep domain knowledge creates durable product advantage.
• Prior exposure to healthcare education, clinical training workflows, or healthcare credentialing.
• Experience owning revenue outcomes, pricing decisions, or a P&L at the product-line level.
• History of operating across multiple customer personas (e.g., institutional buyers, administrators, and end users simultaneously).
• Advanced degree (MBA or related) - not required, but a plus given the strategic and commercial scope of the role.

HIRING RANGE
The current full-time, annualized base pay hiring range for this role is $192,300.00-$275,000.00. In accordance with applicable state laws, we are providing the expected pay range for this position. Individual compensation will be determined by various factors, including relevant experience, qualifications, current business needs and local market factors. Most regular, full-time employees are eligible to participate in an Ascend incentive bonus or sales plan.
BENEFITS

• Health, dental, and vision insurance
• Company paid life Insurance
• 401(k) with company match
• Paid time off and parental leave
• Employee assistance program
• Other wellness programs such as Headspace and Airvet
• Charitable matching program

Fostering A Sense of Belonging
Our values-driven culture unifies our teams and inspires a mindset of action, innovation, and collaboration, with a relentless focus on customers. We seek out and celebrate all people and perspectives and cultivate an inclusive culture where everyone can thrive, feel valued, and be authentic. Our culture is firmly rooted in the belief that by embracing our differences and drawing on diverse perspectives, we are a stronger, more innovative, and more successful organization where employees experience a sense of belonging.
Ascend Learning, LLC is proud to be an equal opportunity employer (M/F/Vets/Disabled). No agency or search firm submissions will be accepted. Applications for U.S.-based positions with Ascend Learning, LLC must be legally authorized to work in the United States, and verification of employment eligibility will be required at the time of hire.