Product Manager — AI-Driven, Multi-Brand Platform Growth

Who We Are

Peaksware is the investment company that owns and operates industry-leading brands MakeMusic, Alfred Music, and formerly TrainingPeaks and TrainHeroic. Our software platforms maximize the potential of expert instructors to reach and impact the lives of the world’s committed performers. We operate at the intersection of technology, finance, and human performance, and we acquire businesses to own and operate them for the long term, not to flip them.

Position Summary

We are hiring a Product Manager to accelerate product development across Peaksware, starting inside Music Brands and expanding to the businesses we acquire next.

For the first twelve months, you will own high-priority special projects inside Music Brands, working monthly on-site with our product and engineering team in Boulder to move important work faster than it would otherwise go. Over the following twelve to eighteen months, the role evolves: you become the product manager we place into newly acquired businesses, arriving early, diagnosing what the product needs, and setting the agenda. This role demands two distinct muscles: the patience to dive deep into technical and domain edge-cases, and the versatility to context-switch across multiple projects and products without missing a beat. You will range across a multi-brand ecosystem rather than staying in a single lane, and you are genuinely energized by dropping into an unfamiliar business, diagnosing what it needs, and driving immediate impact.

Key Responsibilities
Accelerate Music Brands and Financial Analysis (First 12 Months)

• Own High-Impact Platform Initiatives across our Music Platforms: Drive high-priority product initiatives inside Music Brands from definition through launch, in partnership with the Boulder product and engineering team.
• Modernize Core Content Infrastructure for Music Brands: Dive deep into the details of asset production, content ingestion pipelines, metadata structures, and licensing workflows to build scalable, reliable systems.
• Investigate Before You Build: Use customer research, product data, and first-principles reasoning to establish what is actually worth building, rather than working from the existing roadmap by default.
• Earn Engineering’s Trust: Work closely enough with engineers and designers that they want you in the room: clear specs, fast decisions, real understanding of the constraints.
• Ship and Measure: Define what success looks like before launch, then track whether it happened and act on the answer. Partner closely with our Boulder-based engineering and product teams. Win credibility through clear technical specs, deep domain comprehension, and fast, well-reasoned decisions
• Accelerate Financial Analysis through AI-enabled automation and productization.

Product Leadership in Acquired Businesses (12–18 Months Out)

• Identify High-ROI AI Opportunities: Evaluate where AI creates real economic value across our businesses, then drive those opportunities through to shipped, measured outcomes. Build and defend a clear view of where AI changes unit economics and where it is merely noise.
• Step into New Businesses and Diagnose Quickly: Serve as the product manager we place into newly acquired companies. Assess an unfamiliar product, its users, its team, and its economics quickly, then form a clear view on what to fix, what to build, and what to stop. Work with the Head of Product to set product direction during the window when it matters most. We invest for the long run, so make the decisions that compound over years rather than the ones that look good in the first quarter.
• Develop Shared Infrastructure Across the Portfolio: Help build the platform layer every brand draws on such as: shared content infrastructure, data pipelines, and AI capabilities that no single business would justify building alone. Form a view on what should be centralised and what stays brand-specific.

Required Qualifications

• 3–5 years of product management experience at a leading software company.
• A track record of shipping products customers adopted, and the ability to say what you learned when they didn’t.
• Practical AI fluency. Hands-on experience applying modern AI/LLM tools, prompt engineering, or workflow automations to solve real operational, data, or product problems with a clear view on where AI adds real value vs. hype.
• Deep systems and analytical judgment. Proven ability to dissect complex backend infrastructure (e.g., data pipelines, CMS, metadata, or workflow logic) and make decisions grounded in product data, unit economics, and first-principles reasoning.
• Credibility with engineers and designers, earned through clarity and good decisions rather than authority.
• Comfort with ambiguity and unfamiliar domains. This role deliberately moves you between products.
• Based in Boston, in the Seaport office Tuesday through Thursday, with the ability to travel to Boulder, Colorado on a monthly basis.

Desired Qualifications

• Experience as the first or only product manager on a product.
• Experience inside a multi-brand or portfolio company, or through a post-acquisition integration.
• Technical fluency in APIs, product analytics, SQL, or AI-assisted development.
• Interest in music, education technology, or tools for instructors and creators.
• If this role appeals to you and you believe you could grow into it, we would rather hear from you than have you rule yourself out.

All applicants will receive equal consideration for employment regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, status as a protected veteran, or length of time spent unemployed.

The work characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Compensation

We are committed to fair and equitable compensation practices. The annual salary range for this role is $95,149-$158,581. We typically hire at the lower to mid-point of the range, with the top end reserved for internal growth and exceptional performance. Final compensation for this role will be determined by various factors such as a candidate’s relevant work experience, skills, certifications, and geographic location. In addition to base salary this position will be eligible for an attractive performance based variable compensation plan.

Benefits and Perks:

Health

• We offer comprehensive health benefits including medical, dental, and vision insurance; health savings and flexible spending accounts, paid parental leave; and an employee assistance program.
• Additional coverage options including Accident & Critical Illness insurance as well as Hospital Indemnity are also available.

Disability and Life

• We offer several company paid options including Short Term Disability, Long Term Disability, as well as Basic Life Insurance and AD&D.
• Additional coverage options including Employee-paid Supplemental Life Insurance for Employee, Spouse, and/or Child are also available.

Additional

• We offer a 401(K) including a company match.
• We observe 12 paid holidays annually and provide discretionary Flexible Time Off. Employees also receive free access to our products, corporate discounts, and professional development resources.
• Access to the Performance and Recovery Center (PARC), our on-site fitness facility, as well as employee only access to on-site locker rooms and showers.
• Employee only access to secure, indoor bike storage and access to e-bikes exclusively to Peaksware employees.
• Access to our onsite Music and Podcast Studio.

If you require a reasonable accommodation to review our website or to apply online, please fill out our Candidate Accommodations Request Form

Peaksware adheres to the FLSA Exemption Threshold for minimum wage in all states.

Recruiting Agency Notice: We do not accept agency resumes or assistance. Please do not forward resumes to our jobs alias or our employees. We are not responsible for any fees related to unsolicited resumes.