• Lead our Product and Engineering teams, including a soon to be hired product manager, while remaining technically engaged enough to guide architecture, review key technical decisions, and remove roadblocks. • Own execution across the product roadmap and engineering delivery, partnering closely with the CEO and leadership team. • Lead the migration of Clubspeed from an on-premise platform to the cloud. • Improve engineering delivery, quality, predictability, and operational excellence. • Build and execute a customer-focused product roadmap that balances innovation, customer value, and technical sustainability. • Lead our PCI DSS 4.0.1 readiness initiative. • Embed AI into how we build software and operate the business. • Coach, develop, and grow a high-performing Product & Engineering team.

Role Description This is a high-impact role at the intersection of corporate finance, M&A, and strategic execution. On the corporate development side, you'll provide rigorous analytical support across M&A evaluation, investor materials, and capital markets processes. In strategic finance, you'll own the end-to-end strategy and execution of initiatives that convert single-product users into multi-product adopters — one of the company's highest-priority growth levers, given that multi-product users generate ~3x ARPU and meaningfully higher retention. Corporate Development - Build and maintain M&A financial models: three-statement models, DCF, comps, precedent transactions, IRR, and synergy analyses - Track acquisition target universe across digital media, consumer apps, and enterprise SaaS; monitor market activity and valuation benchmarks - Support due diligence workstreams: coordinate information requests, organize data rooms, synthesize outputs across finance, legal, and operations - Prepare investor-facing materials including three-statement projections, KPI decks, board packages, lender reports, and capital raise support (including Series D) Strategic Finance — Cross-Platform Synergy - Identify and size cross-sell opportunities across Outside’s three business units using subscriber data, audience analytics, and product usage patterns - Build the business cases, financial models, and OKR frameworks for approved initiatives; own execution from scoping through results - Manage two to three active conversion initiatives by end of year one, with real-time dashboards tracking ARPU, conversion rates, and retention impact - Prepare regular performance reports for the executive team with clear commentary and recommended next steps Qualifications - 4+ years in investment banking, advisory/consulting, or strategic finance at a high-growth tech or media company - Strong financial modeling skills: three-statement models, DCF, comps, precedent transactions, IRR - Experience supporting multi-workstream processes (M&A, capital raises, strategic projects) with rigorous attention to detail - Advanced Excel (Power Query, VBA); familiarity with PitchBook or Capital IQ; comfort with Tableau or Power BI - AI-native — fluent using Claude/LLMs to accelerate research, analysis, and execution - Preferred: digital media, SaaS, or consumer subscription background; Python or SQL experience; MBA Requirements - What Success Looks Like - 90 days: deep understanding of Outside’s business units and platform thesis; initial cross-platform opportunity assessment delivered; contributing to active M&A or investor materials workstream - Year one: two to three cross-platform initiatives actively managed with measurable ARPU and retention impact; trusted analytical partner to the executive team Benefits - Entirely remote jobs that could be performed in Colorado - Salary range: between $100,000 to $130,000 - Additional benefits include health care, vision, dental, retirement, Flexible Time Away, sick leave, and more

• Running a continuous weekly 1:1 practice, removing blockers, and mentoring a team of engineers on both technical craft and career growth • Establishing career growth objectives, leveling expectations, and providing continuous, specific feedback for every engineer on the team • Reviewing code, design documents, tests, and CI/CD changes regularly, raising the bar on quality, simplicity, delivery speed, observability, and long-term maintainability • Backing up the team in the trenches: pairing on hard problems, jumping into incidents, debugging production issues, writing code, and helping engineers use AI tools responsibly when they improve quality or speed • Driving architectural, tooling, and technical roadmap decisions that improve business outcomes, delivery speed, reliability, and operational efficiency • Collaborating with product, design, and customer-facing teams to connect technical work to revenue, retention, customer experience, and operational efficiency • Planning, managing, and allocating engineering capacity against quarterly OKRs, using business impact, operational risk, and your own understanding of the system to guide trade-offs • Championing and improving Beyond’s engineering practices such as trunk-based development, CI/CD, risk-based testing, feature flags, observability, pairing, code reviews, and collective code ownership • Contributing to new products and projects while supporting and maintaining the existing code base, as needed

• Own the end-to-end strategy and roadmap for all internal tools, platforms, and automation treating internal technology as a product, not a cost center. • Make strategic build-vs-buy decisions, knowing when a custom-built solution creates a lasting advantage and when a SaaS tool is the right answer. • Map current and next-state process flows across the entire internal toolchain and lead systems transformation for internal teams. • Architect and maintain the full engineering lifecycle for internal platforms from ideation and design through deployment, iteration, and deprecation. • Build seamless, API-first ecosystems that integrate internal tools across HR systems, finance platforms, knowledge management, CRM, and developer infrastructure. • Own system reliability and operational resilience: establish success metrics for uptime, performance, and employee productivity. • Design scalable, secure architectures using cloud-native principles, microservices, and modern integration patterns. • Lead the strategy for integrating AI and LLMs into internal workflows reimagining how knowledge is shared, decisions are supported, and work is executed across the organization. • Deploy intelligent automation tools including AI where appropriate to streamline internal processes and improve decision-making. • Evaluate and integrate AI-assisted troubleshooting, proactive recommendations, and intelligent automation into the internal platform layer. • Stay ahead of technology trends and drive continuous experimentation you build prototypes, not slide decks. • Reduce cognitive load for internal users by providing golden paths, standardized workflows, and self-service capabilities. • Ensure frictionless onboarding and seamless integration across the tool ecosystem. • Measure platform success through adoption rates, user satisfaction, DORA metrics, and productivity impact not feature count. • Build, lead, and mentor a high-performing team of engineers and engineering managers. • Cultivate a collaborative engineering culture rooted in ownership, speed, and craftsmanship. • Provide technical mentorship and create growth paths for individual contributors and managers alike. • Foster psychological safety and a feedback-driven environment that empowers people to do their best work. • Partner with People, Finance, Engineering, Legal, and Operations leadership to translate complex business needs into a unified technical vision. • Serve as the bridge between business stakeholders and the engineering team you speak both languages fluently. • Align internal platform investments with broader company strategy and demonstrate measurable ROI.