Real World Practitioners

Best in class transformation advisors, coaches, and consultants

Transformation Expertise, All in One Place

Our advisors are the real deal: they’ve helped companies successfully navigate digital transformations and operating model transformations as employees and as consultants. No one here is new to the game; everyone here has experienced this work first-hand as leaders and change drivers at some of the biggest companies you know. Now they’re focused on helping your company navigate a successful transformation.

Our team is comprised of talented, driven, and accomplished independent consultants across a spectrum of disciplines. We come together to tackle the specific needs of our clients, complementing each other’s talents and personalities to ensure you’re getting the A-team to help you meet your challenges and opportunities, every time.

Our Featured Consultants

  • Jen Swanson headshot

    Jen Swanson

    Jen’s career spans over 25 years of roles in customer relationship management, marketing operations, information technology, and operations management in higher education and healthcare organizations, including the University of Minnesota, Capella University, Children’s Minnesota, and UnitedHealth Group. Her consulting career began in 2019 and in 2023 she expanded that work by creating Tuckpoint Advisory Group.

    Jen’s practice areas include Digital & Operating Model Transformation, C-Suite and Senior Leader Advisory, Product Operations, Change Agility, and Leadership Competencies.

  • Maura Charles Headshot

    Maura Charles

    Maura’s experience encompasses 30 years in digital transformation and product management roles, building and coaching engaged, high-performing digital technology teams for beloved consumer brands that inform and entertain. Her consulting career began in 2021. She is also a writer and brings creative thinking to all she does.

    Maura’s practice areas include Digital & Operating Model Transformation, C-Suite and Senior Leader Advisory, Product Strategy, Product Coaching, Workshop Development and Facilitation.

  • Brent Swanson Headshot

    Brent Swanson

    Brent works at the intersection of people, process, and technology, empowering businesses to quickly mature from operating in chaos to running highly effective and innovative product management practices. He has both created new and grown established brands and products for a diverse range of industries like Be the Match, CaringBridge, Brandpoint, Wells Fargo, 3M, HealthPartners, Land O’ Lakes, Medtronic, Northwest Airlines, and Target.

    Brent’s practice areas include Product Strategy, Product Coaching, Product Operations, Agile Methodologies, and Workshop Development and Facilitation.

  • Summer Miller

    Summer brings 25 years of experience in a Fortune 500 setting, including multiple executive HR positions at U.S. Bank and more recent experience consulting and advising small to mid-sized businesses. She helps leaders and teams design for strategic growth and transformation by integrating people practices, structure, processes, and change leadership. Summer holds a Doctorate in Organizational Leadership and a Master’s Degree in Organizational and Professional Communication.

    Summer’s practice areas include Organization Design, Culture, Change Management, Change Leadership, Team & Strategic Alignment, Talent & Leadership Development, HR Strategy

  • Craig Sicular

    Craig brings 25 years of experience as a trusted business consultant and advisor, helping organizations design and deliver operating models that unlock the full potential of their digital products and teams. With a background that bridges business and technology, he excels at translating customer needs into strategic solutions that drive clarity, efficiency, and engagement across complex organizations.

    Craig’s practice areas include Digital & Operating Model Transformation, Business Process Transformation, Change Agility, and Program & Project Management.

  • Kirsten Hunter

    Kirsten helps product and technology teams build customer-centered strategies that connect business goals to meaningful outcomes. Drawing on more than 20 years of experience leading product and technology initiatives across digital health, fintech, agtech, data, entertainment, and enterprise software, she brings both breadth and depth to every engagement. Kirsten partners with organizations of all sizes to align teams, inspire clarity, and deliver lasting impact.

    Kirsten’s practice areas include Product Strategy, Product Discovery, Product Operations, Agile Methodologies, Team & Leadership Alignment, and Product Mindset Coaching.

  • Krista Stensrud

    Krista is a product strategist, leadership advisor, and transformation coach with nearly two decades of experience shaping, launching, and optimizing digital products across diverse industries. She helps organizations unlock the full potential of their product portfolios by aligning strategy, structure, and culture, enabling teams to set clear goals, make data-informed decisions, and operate with shared accountability.

    Krista’s practice areas include Cross-Geo Operating Model Transformation, Product Strategy, Leadership Coaching, Product Operations, Marketing Planning, Content Strategy, and Workshop Development and Facilitation.

  • Ben Solberg

    Ben is a product coach and consultant with 25 years of experience leading initiatives in product management, marketing, and technology across industries, including financial services, healthcare, manufacturing, and food. A former Vice President of Product at Ameriprise Financial, Ben combines strategic insight with a human-centered coaching approach to help teams strengthen discovery and delivery practices, unlock innovation, and grow their impact.

    Ben’s practice areas include Product Operating Model Transformation and Leadership, Discovery Maturity, Stakeholder Management, Change Management, Leadership and Culture Optimization, and Conflict Resolution.

  • Jesse Rosel

    Jesse is a digital transformation and product leader who helps organizations strengthen product strategy, accelerate delivery, and align teams to deliver value faster and more effectively. With 20+ years at the intersection of technology, design, and business, he guides teams through every stage—from clarifying vision to achieving meaningful, measurable outcomes. Jesse brings a pragmatic, human‑centered approach that simplifies complexity, improves operational performance, and leverages emerging capabilities like generative AI to enhance productivity and decision-making.

    Jesse’s practice areas include Operating Model Transformation, Product Strategy, Product Operations, Change Agility, Leadership Competencies, and Generative AI.