Senior Associate, Strategic Initiatives - Peaksware

Peaksware•Boston, MA

6d•Hybrid

About The Position

Peaksware is the parent company for 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 empower athletes and musicians to achieve their peak potential through data-driven software, robust analytics, and expert-led content. We operate at the intersection of technology, finance, and human performance. As a lean, high-growth organization, we value execution, intellectual curiosity, and radical candor. This is an opportunity to join a category-defining software company at an inflection point where AI is reshaping how every team operates. Reporting to the CFO, the Senior Associate, Strategic Initiatives will serve as a strategic partner to the executive team and leaders across Peaksware’s portfolio of brands, helping drive some of the company’s highest-priority strategic and operational initiatives. This is a high-autonomy, high-impact role for a former top-tier consultant, financial analyst, or strategy and operations professional who enjoys taking ambiguous business problems and turning them into clear analysis, recommendations, and action. The Senior Associate, Strategic Initiatives will work across Finance, Sales, Marketing, Operations, Product, and Engineering to analyze business performance, build financial models and business cases, identify opportunities to improve growth and efficiency, and drive cross-functional initiatives from idea through execution. They will also bring a strong understanding of AI and automation, using these tools to accelerate analysis, improve workflows, and unlock new ways of working across the organization. This role offers broad exposure to the business, meaningful access to executive leadership, and the opportunity to make a measurable impact across the Peaksware portfolio.

Requirements

2+ years of experience in management consulting, financial advisory, corporate strategy, FP&A, or a similarly rigorous analytical role.
Experience in a strategy consulting environment is a plus.
Strong financial and analytical skills: Ability to analyze business performance, build financial models and business cases, evaluate ROI, and turn data into clear recommendations.
Exceptional problem-solving and business judgment: Comfortable taking ambiguous problems, structuring the analysis, identifying the key issues, and determining a practical path forward.
Strong communication and executive presence: Able to synthesize complex information, communicate clearly with senior leaders, and influence cross-functional stakeholders without direct authority.
AI fluency: Demonstrated experience using modern AI tools to improve productivity, analyze information, automate workflows, or solve business problems. You don't need to be an AI engineer, but you should be curious, hands-on, and excited about finding new ways to apply AI.
Bias toward execution and ownership: Comfortable operating with limited direction, rolling up your sleeves, and taking initiatives from analysis and recommendation through implementation and measurable results.

Nice To Haves

SaaS or technology experience, particularly in strategy, operations, finance, or general management.
Experience leading cross-functional strategic initiatives from initial analysis through implementation.
Technical and data fluency, including experience with SQL, Python, APIs, business intelligence tools, or AI-assisted development.
Experience working across multiple business units, brands, or markets, ideally within a portfolio or multi-business environment.
Experience working directly with executive leadership and supporting high-level strategic decision-making.

Responsibilities

Partner with Executive Leadership: Work directly with the CFO and executive team on high-priority strategic questions and decisions across Peaksware and its portfolio of brands.
Turn Ambiguity Into Action: Take complex or loosely defined business questions, structure the problem, run the analysis, and deliver clear recommendations and a path forward.
Prepare Executive Insights: Produce concise analyses, business cases, and presentations that help leadership evaluate opportunities, track initiative progress, and make informed decisions.
Find the High-Value Use Cases: Evaluate where AI and automation can meaningfully improve productivity, decision-making, and business processes across the organization.
Build and Prototype: Use modern AI tools to rapidly build agents, scripts, internal tools, and workflow automations that solve real business problems — and apply those same tools to your own analysis, research, modeling, and reporting.
Scale Adoption: Partner with Engineering, IT, and functional leaders to deploy what works, raise practical AI fluency across teams, and drive adoption.
Lead High-Impact Projects: Own 1–2 high-priority cross-functional initiatives at any given time, from initial analysis and recommendation through implementation — coordinating across functions and driving accountability and follow-through.
Redesign How Work Gets Done: Work with functional leaders to identify inefficient, redundant, or manual processes and determine the right fix: redesign, technology, automation, or elimination.
Solve Cross-Brand Problems: Identify where shared processes, technology, data, and capabilities can be leveraged across Peaksware's brands, building the relationships needed to surface and scale them.
Measure Impact: Set clear success metrics for strategic initiatives and track results so investments translate into measurable business outcomes.
Analyze Business Performance: Evaluate financial and operational performance across brands to identify trends, risks, and opportunities to improve growth, profitability, and efficiency.
Support FP&A: Partner with Finance on forecasting, budgeting, variance analysis, scenario modeling, and recurring reporting for leadership.
Build Business Cases: Develop financial models and ROI analyses to evaluate investments, headcount, technology, and other strategic decisions.

Benefits

Comprehensive health benefits including medical, dental, and vision insurance
Health savings and flexible spending accounts
Paid parental leave
Employee assistance program
Accident & Critical Illness insurance
Hospital Indemnity
Short Term Disability
Long Term Disability
Basic Life Insurance and AD&D
Employee-paid Supplemental Life Insurance for Employee, Spouse, and/or Child
401(K) including a company match
12 paid holidays annually
Discretionary Flexible Time Off
Free access to our products
Corporate discounts
Professional development resources
Access to the Performance and Recovery Center (PARC), our on-site fitness facility
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