Product CV

Jake Shepherd

Head of Product · Creative Director · Product Design Leader. 20+ years bridging creative direction, product strategy, and hands-on delivery. Specialist in 0-to-1 product development: customer discovery, MVP scoping, rapid prototyping, and the sustained execution required to reach product-market fit.

Profile

Product and design leader with a rare combination of deep design craft, commercial acumen, and genuine technical fluency — comfortable in a Figma file, a sprint planning session, or an investor meeting. Most recently Head of Product at Entelechy Academy (SaaS, HR/edtech), on SLT and driving 500% user adoption growth. Previously co-founded Folio Mirrors, building interactive touchscreen hardware/software products across retail, beauty, and fitness. Currently integrating AI-assisted workflows across product development, content strategy, and operational tooling.

Notable Achievements

Professional Experience

Head of Product · Entelechy Academy Ltd

2020 – 2026 · SLT · B2B SaaS, character assessment & team analytics

  • Member of SLT, responsible for overall product strategy, roadmap, and execution for a disruptive HR-tech platform.
  • Led a team of 2 Product Owners, design, data & insights, and DevOps.
  • Drove user adoption by 500%; reduced DevOps costs by 30% MoM; improved time-to-launch by 50%.
  • Owned roadmap, prioritisation, and stakeholder communication across leadership and the wider business.
  • Implemented in-app subscription flows and SaaS pricing tier architecture.
  • Led event tracking implementation using Segment and PostHog; built user subscription modelling from scratch.
  • Managed RFP for offshore development team; led hiring of onshore team.
  • Used market insights and competitor analysis to shape KPIs and inform roadmap decisions.
  • Participated in sales discovery meetings and investor engagements.

Head of Design · Entelechy Academy Ltd

2019 – 2020 · Design lead, foundational UX and visual language

  • Joined as design lead to define the product's visual language and UX foundations ahead of broader scaling.
  • Led the creative team through early-stage product iteration, establishing design systems and a human-first approach to complex data and insight presentation.

Design & Product Director · Folio Mirrors Ltd

2017 – 2020 · Interactive touchscreen mirror startup · 0-to-1

  • Led product development and ownership integrating ML face recognition and AR across hardware and software.
  • Developed three MVPs across retail, beauty, and fitness verticals.
  • Managed product strategy from concept to market launch (0 to 1); achieved revenues of £200k+ YoY.
  • Shipped 30 units globally in 18 months — Footlocker retail activation, Clinique beauty activation, Condé Nast New York activation.
  • Ensured product flexibility across deployment environments: standalone Linux application and browser-based web app.
  • Hands-on across rapid prototyping, developer collaboration, sales events, and investor demos.

Creative Director & Director · MSDC

1996 – Present · Design and brand strategy agency

  • Led creative and strategic direction for clients including Telefónica, Rio Tinto, Hammerson, and Four Seasons Hotels.
  • Managed regional below-the-line campaigns for property firms across Liberty Romford, The Bentall Centre Kingston, Shires Leicester, and others.
  • Led multi-stakeholder projects for shopping complex launches, working with asset management and marketing teams.
  • Grew the business through hiring and nurturing talent across design, client services, and support.
  • Led accounts representing in excess of £10m annually.
  • Dedicated pro bono creative work to Darent Valley Hospital's charitable campaigns (Little Buds, The Lollipop Appeal).

Technical Skills

Product & Methodology
Scrum · Agile · Waterfall · Event Modelling · Subscription Modelling · OKRs · Jobs-to-be-Done
AI & LLMs
Claude (Anthropic) · ChatGPT · Cursor · LM Studio · Prompt Engineering · AI-assisted product workflows · AI-augmented design and development
Design & UX
Figma · Adobe Creative Suite (Expert) · UX/UI Design · Design Systems · Rapid Prototyping · Branding & Brand Strategy
Frontend Development
React · TypeScript · Tailwind CSS · HTML · CSS · JavaScript
Backend & Infrastructure
Supabase · AWS · GitHub · Cloudflare · MS Exchange (Enterprise Admin)
Analytics & Data
Segment · PostHog · Mixpanel
Project & Product Management
Notion · Asana · JIRA · Slack · Linear

Special Projects

  • Ocean Finance TV Commercial — directed and produced the first-ever television commercial for Ocean Finance.
  • 2012 Olympic Relay Cauldron — designed the cauldron handed between Bell Telecom and BT during the London Games sponsorship hand-over.
  • Digital Ribbon (O2) — creative direction for a large-scale experiential installation.
  • Filmmaking — started with Bolex 16mm film; has written, directed, and produced 10 short films.