Spotlight On: Jen Swanson, Founder & Principal, Tuckpoint Advisory Group

Spotlight On: Jen Swanson, Founder & Principal, Tuckpoint Advisory Group

2023-02-21T10:55:14-05:00February 21st, 2023|Economy, Minneapolis-St. Paul, Professional Services, Spotlight On|

4 min read February 2023 In an interview with Invest:, Jen Swanson, founder and principal of Tuckpoint Advisory Group, discussed key milestones and differentiators for the firm, common mistakes that prevent companies from fully leveraging their technological investments and how to avoid them.

What have been some of the key milestones for Tuckpoint Advisory Group during the past year?

In 2022, my consultancy had a big turning point. I’ve been in practice since 2019, just before COVID hit, which was terrifying at the time but, in retrospect, it was the best timing for the kind of consulting I do. I focus on digital transformation and helping organizations reorganize themselves by shifting their structure, funding models, governance, culture and talent to better adapt to digital transformation and the shifts that a digital world demands. I was fortunate to have a six-month runway before COVID hit and lots of companies used the pent-up energy and resources to win in the new environment through digital transformation. The realization in COVID was that an org had to transform lots more than just their tech in order for a digital transformation to be successful.

In the first two years of my consultancy, I was mainly helping with product strategy and market fit but in 2021, I shifted my focus upstream to helping organizations understand why their investment in technology wasn’t showing any real value. I pivoted from focusing on just the technology and digital experience to looking at the C-Suite and the organizational dynamics that were preventing them from transforming in a digital marketplace. I’ve been independent for the past four years and have worked on small project teams but now my focus is scaling and delivering through partnerships so I can better meet the needs of larger enterprises. I’m starting to work with specialized people in HR, change management and coaching to bring a more united approach and cater to each company’s unique needs.

What sets your firm apart from other consultancies?

We offer a bespoke model. It’s not a one-size-fits-all approach like buying a jacket off the rack. Instead, there is a balance between custom solutions and proven frameworks, best practices and patterns. We don’t follow a 27-step process like some big box consultancies but we also don’t reinvent the wheel each time. We aim to find the sweet spot between these two approaches.

When we approach a project, we consider the best practices, industry trends and how digital transformation is taking shape in different types of companies, such as financial services, healthcare, manufacturing and media organizations. We understand the unique organizational and business transformation drivers for each company, including the impact of culture and history. Our goal is to find the balance between a set plan and figuring it out as we go, while also embedding ourselves with our clients.

We provide more than just advice. We embed with our clients and help them implement our recommendations. It’s a learning-by-doing approach where our consultants take the lead at first but, over time, the client moves into the driver’s seat. Unlike some consultancies, we don’t hand over a $1 million PowerPoint at the end of our engagement and leave the client unsure of how to execute it. Our goal is to make our recommendations a lasting reality within the organization. That’s our sweet spot.

What are some of the strategies that clients can incorporate to take full advantage of their technological investments?

The biggest trend I see often is that in the past, technology investment was made in a haphazard manner. Often, the decision is made within business leadership to implement a tech solution, with no input or alignment with their technology partners. They ink deals for platforms, solutions or apps  without considering their integration with the company’s data systems, legacy platforms, or existing experiences. This results in the IT team being handed the task of implementing the technology without being part of the decision-making process. We call this “throwing it over the wall” and it’s the number one behavior we’re trying to put an end to.

In a modern organization, business and IT teams work together in a strategic partnership, rather than having business teams making decisions and IT teams just executing them. This shift in thinking usually starts with a change in the C-Suite, usually when there’s a new leader in the tech organization who’s willing to go to bat for a more strategic role in the company. However, the change cannot just be decided at the top; it requires restructuring teams, culture and ways of working to realize the full potential of technology and its ability to drive business strategy. That’s where my consulting services come in, to help organizations make this transition.

What is the role of coaching and mentorship in the digital transformation process? 

I have been passionate about mentorship for a long time and used to run mentor programs earlier in my career. It has always been a foundational tool in my toolbelt that leaders should use to grow and nurture talent within an organization. Whether it’s through formal or informal mentoring relationships, such as between a lower-level employee and a higher-level one, or peer mentoring across the organization, this cross-functional exchange is necessary as no job exists in a silo anymore. People in business need to understand IT, IT needs to understand finance and finance needs to understand operations. It is all connected, and mentorship can help tremendously in this area.

As a blanket statement, I am a huge fan and advocate of mentorship – every company, every industry. But I also am a vocal advocate for women in business and technology, especially in terms of creating mentorship and sponsorship relationships to help women in lower and middle management progress into leadership positions. Mentorship is critical in my opinion. 

But mentorship and coaching is also a tool we deploy in our consulting work, to great success. For example, we may be asked to work with chief product officers or people new to product leadership to help them navigate the shift from a traditional, linear project management approach to a more nimble and agile product management model. We also use mentorship and coaching techniques to help leaders understand how to present their portfolios in a way that is empowering to their teams, and we coach executives on how to lead differently in transformed organizations. Many C-Suite leaders have never led in an agile organization and coaching helps them make this shift by showing them the way and helping them ask the right questions.

What are your top priorities?

My top priorities revolve around finding organizations, particularly in regulated and legacy industries, that have successfully used a traditional operating model but are now realizing they need to adapt to compete in new areas. These companies compete for talent who expect autonomy and the ability to work in an empowered way, not just as order takers. To help these organizations succeed in the future, my consultancy is focused on bringing in modern operating models from the tech industry and applying the best elements to these legacy companies. I want to be part of the continued transformation and ensure that beloved brands in the Midwest don’t suffer the same fate as Kodak or Blockbuster. In the next two to five years, my consultancy will be focused on helping these kinds of companies achieve continued growth.

For more information, visit: