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Stephen DaglessSD

Stephen Dagless

Product Strategy, Operations and Roadmapping

€984/day
Bath, GB
15+ years

Average response time: 1 hour

About Stephen

I help organisations turn strategy into delivery with clarity, focus, and measurable outcomes. With over 15 years’ experience across industries including retail, technology, finance, government, and education, I bring both breadth and depth in product management, roadmapping, and strategic delivery.

I work with leadership teams to define vision, translate it into actionable roadmaps, and put in place the processes and tools that keep teams aligned and accountable. From designing OKR frameworks and setting up Aha! roadmaps, to creating reporting models and operating rhythms that actually work, I focus on the detail that makes strategies executable.

What makes me different is the combination of hands-on product expertise and executive coaching skills. I not only help teams design the right approach, but also support leaders to grow the confidence, communication, and clarity they need to lead effectively. This balance of delivery know-how and leadership development means I can help at multiple levels of an organisation - from fixing process bottlenecks, to shaping strategy, to coaching executives through complex decisions.

I’ve partnered with start-ups finding product-market fit, scale-ups needing structure, and large enterprises managing global portfolios. Typical projects include:

Product strategy and roadmapping design

OKR implementation and alignment

Aha! administration, configuration, and training

Portfolio and delivery operating model design

Executive coaching and leadership development

Clients value my reliability, responsiveness, and ability to cut through complexity.

If you’re looking for someone who can combine product management expertise with leadership coaching to deliver practical results, I’d be glad to help.
  • English

    Native or bilingual

Can work on-site
Bath (up to 50km)

Experience

  • Your Roadmap Coaching & Consulting
    Founder, coach and consultant
    DIGITAL AND IT
    October 2021 - Today (4 years and 8 months)
    Bath, England, United Kingdom
    Helping product leaders and business deliver what matters most by aligning strategy and delivery, tooling, processes and most importantly, mindset.
    • Product strategy, operations and roadmapping consultancy
    • Aha! Roadmaps (and full product portfolio) implementation and training
    • Senior and executive coaching
    Product management Executive Coaching Leadership OKRs & SAFe Aha! Roadmaps
  • Aha!
    Snr Manager, Customer Success
    DIGITAL AND IT
    January 2017 - September 2021 (4 years and 8 months)
    Bath, UK
    Aha! is a different kind of high-growth SaaS company. We are the world's #1 roadmap software and help people achieve their best. Over 5,000 enterprises and 500,000 product, innovation, and engineering leaders trust our software to build lovable products and be happy doing it. We are self-funded, highly profitable, always distributed, and have no sales team. Aha! is recognized as one of the best companies in the U.S. to work for and we have donated nearly $1 M to people in need through Aha! Cares. Learn more at www.aha.io.
    Training Customer Success Product management Aha! Roadmaps SAAS
  • TransVault Software
    Director of Product Management
    DIGITAL AND IT
    July 2012 - December 2016 (4 years and 5 months)
    Bristol, United Kingdom
    TransVault is the worlds first and leading vendor of automated email archive migration software. Distributed through a global channel of partners, TransVault products enable the strategic objectives of the worlds largest and medium sized Enterprises.
    The role of Director of Product Management involves working closely with partners, customers, the senior management, sales & marketing, and engineering teams to develop product strategy and lead its execution - a leadership role with significant visibility and accountability.
    Product management Product operations & roadmapping Leadership SAAS

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Education

  • 7 diploma
    7 diploma
  • PGCE:FE, Post 16 and Adult Education
    Nottingham Trent University
    2000
    PGCE:FE, Post 16 and Adult Education

Skill set

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