Spotlight On: Jen Swanson, CEO & Principal, Tuckpoint Advisory Group
July 2024 — In an interview with Invest:, Jen Swanson, CEO and principal of digital transformation consulting firm Tuckpoint Advisory Group, discussed the significant growth and trust built with clients over the past year, emphasizing a shift toward operational model transformation at technology enabled companies. Its approach focuses on articulating strategy in terms of outcomes, organizing work around those outcomes, and embedding senior consultants as partners with client leadership to drive transformational change.
What have been some of the firm’s accomplishments from the last year?
When we last spoke with Invest:, we were just starting, having just launched the brand into a boutique firm. Since then, we have grown quite a bit. We now have 10 consultants on a myriad of projects with some really exciting companies. What I am excited about is the solidification of that growth since it is now starting to feel tangible and more substantial. That is due to the trust we have in our clients and the trust that they have in us. We can only go as fast as our clients want to go because the work we do is not always easy and requires vulnerability and peeling back layers and doing that messy work. Finding companies that have been willing to go there with us has been satisfying and exciting.
How do you approach adopting digital transformation?
When we go in, it is usually under the circumstances of digital transformation, but really what we do is operating model transformation. The last 15 to 20 years of digital transformation has been what I call the first wave of digital transformation because it is all about the tech. The way I define digital transformation is about organizations putting technology into every corner of the business to see how it can enable the full end-to-end aspect of the business no matter what industry.
For most companies that first wave has been taking that technology and putting it on top of established structures and ways of working that often results in friction and lacks that seamlessness that clients are looking for. The second wave of digital transformation is about addressing the operational constraints, which is where we come in. That usually surprises our customers because we don’t care as much about the technology as much as we do about how your organization is structured, how your teams are organized, how your strategy is articulated in terms of outcomes, and how you are funding and governing teams. If these things are not addressed you will never get the full ROI on your technology investments. That has been a revelation to clients and more people are realizing that putting new tech on old ways of working is like putting lipstick on a pig.
What is the methodology for driving business transformation?
No two approaches look the same and we believe we are the anti-consulting company in that way because we don’t have a single framework, but rather we can identify and follow some predictable patterns. We start by looking at strategy and whether or not it’s articulated in terms of outcomes or outputs. Many companies have traditionally articulated their strategies from outputs and we help them refocus by aiming toward particular outcomes like growing a segment or improving a particular experience. Strategy articulated as outcomes is not as easy as it sounds and is much harder to wrap your brain around because it is not how they have done it before. But, it is a very important place to start; to begin moving from output to outcomes in a way that isn’t just a one-off but to shift the entire organization to prioritize outcomes.
The second part organizes work (and money) around those outcomes and focuses on those segments to move them forward significantly, instead of spreading the funding evenly throughout the business so that everyone moves the marker by 1%. That comes with a lot of organizational structure, team and role definition, as well as product management, agile delivery and dev-ops. The outcomes and prioritization are the big buckets we work on depending on what stage a business is at by the time we start working together.
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How does transformational leadership play a role in your initiatives?
Our model is very much to embed with our clients. Our consultants are all senior consultants and have all been on the corporate client side before, often in leadership roles. Usually, one of us partners with executive leaders to be an advisor and someone they can go to for those worries and fears about the business. That approach has really worked for us and is a motivator for our consultants because they want someone else to benefit from the experience and struggles they themselves have been through.
How do you stay ahead of emerging trends to integrate them into your services?
The reality is that there is always going to be something new. I think what we care about more is if we have curious people with a growth mindset, rather than technology experts. If you try to stay ahead of the game on technology skills you will always be behind because the next thing will come and then you won’t have those people on your bench. AI for example ramped up quickly. If you don’t have people willing to learn when something new arises then you are going to be dead in the water. That is why for us technical skill is less important than curiosity and willingness to learn.
How do you foster a culture of innovation and collaboration within the team?
Some of it is trial and error and some of it is hard because we do not have a physical office that we come into. Everyone is remote and mostly in different time zones. We try to gather together when possible. I try to remind people that we have each other and everyone has a unique perspective or idea they can share. We use platforms like Slack and Teams to create the space for that collaboration and camaraderie, and it does work.
What is your near-term outlook for the firm?
We want to continue growing. We’ve been on a steady growth trajectory for the last five years, and if we can keep that going, I’d be very happy. In terms of ambitions, our mission is to do interesting work with clients that are committed to transformation so we can continue to be a great place to work for consultants and a great partner to our clients.
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