Overview

Job DescriptionJob DescriptionWho We ArePeaksware 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.Position SummaryReporting 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. This is a hybrid role based in our Seaport office in Boston, MA, with an expectation of being in the office three days per week (Tuesday, Wednesday, and Thursday).Key ResponsibilitiesStrategic & Executive Support 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.AI & Automation 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.Strategic & Operational Initiatives 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 f