A Year of Hitting Stride: SSC Leadership Looks Back on 2024

In 2024, SureSwift implemented several strategic changes to its operational frameworks. We welcomed some accomplished new talent to our team and fine-tuned our approach to managing and scaling B2B SaaS businesses. The result? A stronger portfolio, consistent high investor returns, and a solid base for continued success in the year ahead.

In today’s article, we sit down with SureSwift Capital CEO James DeGreef to reflect on the wins, lessons, and breakthroughs that defined 2024. We’ll explore how the adoption of a new set of operational strategies within SureSwift has fostered growth and encouraged greater collaboration among our portfolio businesses.

But before we get started, we’d like to take a moment to introduce you to the six new leaders joining us at SureSwift, each of whom brings exceptional expertise and vision to our company:

Julien Francois: Chief Financial Officer of SureSwift Capital, Victoria BC

Julien Francois, the new Chief Financial Officer of SureSwift Capital, is a seasoned financial executive with over 15 years of experience across diverse industries, including technology, digital media, and mining, and expertise in M&A, FP&A, and tax.

Natalie Arseneau: Director of Investor Relations of SureSwift Capital, Victoria BC 

Natalie Arseneau bridges the gap between financial insights and strategic communication, fostering strong relationships with our investors and driving transparency. With a career spanning senior management roles in public and private companies across the innovation sector, she brings a blend of financial acumen, operational understanding, and a passion for storytelling. 

Justyn Maglalang: General Manager of Ghost Inspector 

Justyn Maglalang, the new General Manager of Ghost Inspector, is a seasoned Operations and Technical leader with over 15 years of experience driving growth, efficiency, and innovation across industries. In this role, he leverages his expertise in digital transformation, operational excellence, and leadership to develop sustainable and data-driven growth. 

Emily Mathison: General Manager of LeadDyno

Emily Mathison, the new General Manager of LeadDyno, is a strategic leader with a passion for helping B2B SaaS companies scale revenue sustainably. She has spent her career finding product-market fit, optimizing sales and marketing strategies, and fostering high-performing teams. 

Mike Anderson: General Manager of Vitay 

Mike Anderson brings over a decade of sales leadership and strategic expertise to his role as the new General Manager of Vitay. Previously, he honed his experience at Operto Guest Technologies, where he built high-performing teams and developed scalable solutions in fast-paced environments.

Lacey Sheardown: General Manager of MeetEdgar 

Lacey Sheardown brings over 20 years of marketing and leadership experience to her new position as General Manager of MeetEdgar atSureSwift Capital. Her enthusiasm, creativity, and growth marketing mindset position her perfectly to lead the MeetEdgar team and expand its loyal customer base.

We’re pleased to welcome these talented leaders to SureSwift, and we’re already seeing the positive impact of their contributions. We look forward to what 2025 has in store for their teams and for all our portfolio businesses.

And now, we invite you to join us for an exclusive conversation with our CEO, James DeGreef.

Reflecting on 2024: Insights from SureSwift CEO James DeGreef

Thanks for sitting down with us, James. How has this second year with SureSwift differed from your first?

My second year has been notably different. Not only did we make some exciting updates to our team, bringing some really talented folks on in key leadership roles, but we also operationalized many of the foundational practices we laid down in 2023. We spent a lot of last year measuring and iterating on what worked, making little pivots toward improvement as we went.

For instance, in 2023, we developed the Exceptional Operator Framework (EOF), which includes our monthly base camps and quarterly business reports. We were then able to refine the framework in 2024 and institute it across all our portfolio businesses. We also created a new set of Core Values and embedded them into everything we do, from hiring and onboarding to business strategy and team management. 

Another major addition to the EOF in 2024 was the introduction of the OKR (objectives and key results) framework. We worked with all our GMs to identify and track OKRs for their businesses. In B2B SaaS, as you’d expect, the OKRs typically revolve around top-of-funnel initiatives, conversion rate optimization, customer expansion, churn reduction, and similar goals. But we also included OKRs focused on product and team initiatives where they made sense. GMs tracked their progress, and we reviewed these OKRs during our monthly business review meetings. This process was a great source of strategic collaboration between SSC Corporate and our portfolio businesses.

In a nutshell, 2024 was spent refining and integrating our practices, turning groundwork laid in 2023 into consistent operational excellence. 

How does the current outlook for 2025 contrast from how things looked at the start of 2024?

Heading into 2025, we’re in a stronger position compared to where we were a year ago. We have an excellent team across our businesses, and John Austin and I are excited about working more closely with our business leaders and the new leaders we brought on this past year, each of whom brings their own distinctive experience and perspectives. Their insights are already making an impact, and we’re looking forward to collaborating with them more. 

Another important area of focus for us in 2025 has to do with AI development within our portfolio businesses. In 2024, we saw some great advancement, particularly with DocParser AI, which introduced some powerful new features through AI like handwriting parsing, checkbox recognition, and resume parsing and databasing. We also began embedding AI into some of our other B2B SaaS products. This year, we’ll be doubling down on those efforts, taking a measured, ROI-driven approach to scaling AI across our portfolio. 

As well, the introduction of OKRs in 2024 brought a more strategic focus to our monthly reviews, helping to align initiatives across all of our businesses. Compared to 2024, where we were setting the stage, 2025 is about accelerating our progress. We have a stronger team, clearer strategies, and the tools to execute at a higher level. I’m very optimistic about what’s ahead.

As CEO of SureSwift Capital, how has your own mindset evolved over the past year?

I’d say I’ve gained a lot more confidence over this last year, largely because of the deeper experience I’ve had working with our leaders and teams. It takes time for people to really gel as a team, and you see that progression through what’s often referred to as the "Forming, Storming, Norming, and Performing" stages. I don’t think we had too much "storming," but I do feel that over the past year, our team—both the corporate team and the business leaders—has really hit its stride.

One highlight from this year that made quite an impact on our company was our first-ever SureSwift Capital Leadership Summit, which was held in Mexico in March. While video calls and remote-first operations are efficient, they can end up feeling somewhat lacking in the humanity department. Meeting face-to-face allowed us to get to know each other on a more personal level. It built a lot of trust, and that’s played a big role in how well the team has come together since.

Interestingly, even the challenges around travel ended up turning into a kind of team-building experience. Some of our team were forced to deal with flight cancellations – some more than one, actually – and though it was frustrating, it ultimately became even more of an opportunity to embrace flexibility and lean on each other. By the time we all made it there, it already felt like we’d accomplished something together.

During the summit itself, several leaders presented on their businesses, sharing their own unique insights and learnings. It was like a condensed version of our Exceptional Operator Framework, packed into a week of content, collaboration, and really good Q&A sessions. The information shared was valuable, but the biggest takeaway for me was the human side—getting to know everyone as three-dimensional individuals.

Looking ahead, we’ve got an exceptional team, strong businesses, and solid plans in place. So the confidence I feel comes from knowing that the team is ready to tackle challenges together. It’s a very different place from where we were a year ago, when we were still in the early stages of forming and figuring things out.

What are some of the big wins of 2024?

One major win this year has been how the company successfully navigated the transition of some major leadership roles. For example, our previous CFO, Paul Moore, made the decision this year to move on from SureSwift. Paul brought a strategic and analytical mind to everything he touched – he was a great leader and teammate. John and I are sorry to see him go, but we’re thrilled to have Julian Francois join as our new CFO. He’s different from Paul but every bit as capable, and he’s been a fantastic addition to the team. Changing a CFO is a big deal for any company, especially in a finance or private equity-focused business, but we managed it smoothly without dropping any balls.

Another big win was leveling up our investor relations, particularly with Natalie Arseneau joining the corporate team. Natalie has taken what was already strong and leveled it up even further when it comes to engagement and communication with our investors.

We’ve also brought on several incredible new portfolio business leaders this year. They bring not only a wealth of experience in team leadership but also their own fresh perspectives, which has been energizing for the company. A lot of credit for that goes to Amanda McKay and our People Ops team, who’ve done an outstanding job finding and onboarding great candidates.

In early 2024, we announced a new set of company Core Values. How have they changed the way SureSwift does business?

The new Core Values have been particularly impactful in how we engage with our business leaders. This year, we’ve leaned on the Values a lot in our discussions with GMs, but we’ve also been mindful not to be too prescriptive about them. Each of our portfolio businesses has its own unique culture and team dynamics, so we’ve left some flexibility for business leaders to implement the Core Values in the ways that work best for their team.

One of the Values that seems to resonate most across the board is "Win Together." It’s become a central theme in how we operate. Everyone brings different strengths and plays different roles, so focusing on relying on and supporting one another to achieve a common goal has really brought people together.

The values of "Integrity & Accountability" have also been meaningful, especially with our investors. In 2024, we introduced quarterly LPAC (Limited Partner Advisory Council) meetings for Fund B, which involve seven investors with diverse experience reviewing portfolio results, asking tough questions, and offering their insights on portfolio strategy. Our investors have appreciated our openness with both successes and challenges. We don’t try to mask if challenges arise with any particular business, and that transparency has helped reinforce trust and accountability.

Of course, we aren’t perfect, so there are some values that are currently more of a work in progress. For instance, we made some headway with being "Data-Driven" as a company this year, but there’s still room to grow, and that’s another point of focus for this year. 

What excites you about what’s next for SureSwift?

I’m excited about the opportunity to start acquiring great new businesses. We’ve been speaking with entrepreneurs and exploring a number of businesses, and it looks like 2025 is shaping up to be a great year to add some awesome new B2B SaaS companies to our portfolio.

Over the past couple years, we’ve gained a lot of intel about what works well and what doesn’t across our portfolio. We ran a systematic review of all our businesses, and now we have a clearer focus on the types of companies we want to acquire going forward.

We’re primarily looking for mission-critical, workflow-based B2B SaaS businesses. These are tools that are deeply embedded in mid-market or enterprise workflows and are incredibly sticky, because they’re so integral to operations. For example, tools like Docparser or LeadDyno, which are both embedded in complex workflows for larger companies. These are solutions that, once implemented, they’re hard to replace because they’re so core to the way businesses operate.

What we’ve found is that while “nice-to-have” software can still add value, mission-critical solutions that are ingrained in daily workflows offer more stability and growth potential. That’s where we’re putting our energy: on finding the types of businesses that solve essential problems and have strong growth trajectories.

Conclusion

As we step forward into 2025, SureSwift Capital is set to continue building upon the growth of the last two years, guided by a clear vision and an exceptional team. Driven from the leadership of James DeGreef, John Austin, and now with Julien Francios joining, the company has progressed from laying a solid foundation to operationalizing key strategies across its portfolio. These initiatives, combined with advancements in AI and thoughtful leadership transitions, have set the stage for a year of growth and advancement. 

SureSwift’s Executive Chair, Don Wharton speaks eloquently on SureSwift’s trajectory: 
"Over the past two years, we’ve been laying the groundwork for something much larger—testing, refining, and strengthening our processes to build a foundation that’s as solid as it is innovative. As we look ahead to 2025, we’re not just preparing for what’s next; we’re actively shaping it. The next chapter of SureSwift is about to unfold, and it’s going to be exciting.”

With strengthened collaboration among the portfolio businesses and a targeted focus on acquiring mission-critical SaaS businesses, SureSwift is primed for expansion in 2025. Here’s to a productive year ahead!