Tuckpoint’s Formula
We take your transformation personally.
THE TUCKPOINT DIFFERENCE
Modernizing your organization isn’t simply about adopting new technologies and digitizing your offerings. What actually moves the needle is a lot more complicated. To help you get the ROI on your technology investments, our experts embed themselves within your teams to evolve how work gets done, shift the cultural behaviors and attitudes around change, and develop a structure that supports continued evolution even as the competitive landscape and product experience changes.
We Build Structures
It begins by elevating the people, systems, and processes to achieve a successful transformation. And it’s sustained by embedding new ways of working within the DNA of the company and the individuals that are the lifeblood of the organization.
We Put People First
We understand that true transformation centers around people—from your internal teams to the customers you serve. Our approach emphasizes 'people-first transformations,' ensuring that technology serves as a tool to enhance human interaction and system support, rather than being the sole focus.
We tailor to your goals
We’ll come to the table with experience, proven methods, and a trusty playbook. Then, we focus on crafting tailored transformation solutions that perfectly align with your specific needs. There’s no one-size-fits-all model, nor is there a need to reinvent the wheel.
WE’VE GOT YOUR BACK
Our team of digital transformation experts knows exactly how to navigate the subtle structural and cultural changes that drive the adoption and impact of new technologies inside and outside of an organization. We sit alongside you to take on the operational challenges that help companies sustain their transformations. And we know we've done our job when your organization can step confidently into the future you've envisioned with teams and structures that can adapt to evolving customer expectations.
Along the way, we bring joy and optimism to the challenging work, making even the most difficult situations seem manageable. Because we've seen and done it all before.
OUR FOUNDER
Meet Jen Swanson, founder, Digital Transformation Advisor, and backbone of Tuckpoint. With more than 20 years in roles across customer advocacy, marketing, technology, and service channel operations, she has a long paper trail of client success stories. Jen also has a knack for reading the room, gaining trust among leaders and internal teams alike, and deploying the right balance of EQ and IQ for maximum effectiveness. Her insatiable curiosity for technology and drive to use it to find innovative solutions to business challenges is infused in the very fabric of our company.
OuR Team
Our team is comprised of talented, driven, and accomplished independent advisors 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.
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 Featured Consultants
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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.
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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.
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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.
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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
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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.
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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.
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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.
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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.
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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.