Piecing Together the Growth Puzzle: Insights from the 2024 SureSwift Capital Leadership Summit

This past March, the portfolio business leaders, corporate team and executive leaders of SureSwift Capital came together from across the globe for the inaugural SureSwift Capital Leadership Summit. The Summit entailed three days of collaborative workshops, illuminating presentations, and team-bonding activities. Presentation topics spanned a variety of subjects, from the particulars of SaaS pricing strategy to the practice of active listening to an in-depth exploration of SureSwift's revised Core Values.

The overarching goal of gathering the SSC SaaS leaders in person was to strengthen relationships and trust across the portfolio businesses, while simultaneously integrating the corporate team as collaborative partners. The Summit was a major investment in professional development and learning for the business leaders, creating additional opportunities for SSC corporate to support each leader in the advancement of their work. Given SureSwift's global remote employee structure, this face-to-face forum was especially beneficial for fostering personal connections and facilitating effective brainstorming and problem-solving.

Over three days, the leadership and corporate teams worked to assemble the puzzle for growth and success through presentations, team-building and solo activities, small group work, 1-on-1’s, executive Q&A’s, and cross-collaboration among portfolio business leaders.

Read on for a breakdown of the three-day Summit. 

Day 1: Living out the Core Values through collaboration, connection, and candor 

Though the Summit began with a series of unfortunate travel events – from delayed flights to lost luggage to complete travel cancellations – it also presented the team with the opportunity to address adversity collaboratively. Put into practice, this meant an emphasis on flexibility and inclusivity as schedules shifted and expectations changed.

Day One began with the creation of a Summit Charter, led by Director of People & Culture Amanda McKay, in which the leaders aligned on purpose, mindset, and commitment. Then, CEO James DeGreef, COO John Austin, and CFO Paul Moore chose to kick off the Summit presentations in non-traditional fashion:

“Typically, when an executive team offers an opening statement, you might expect a sort of straightforward ‘talking heads’ welcome,” shares SSC Director of Marketing Tracie Clayton, “But instead, James, John, and Paul sat down in front of everyone and began fielding questions. They turned what could’ve been prescriptive instructions – ‘this is how this will go’ – into a candid and open conversation that immediately generated deep and important questions. And that carried over and set the tone for the entire Summit, because it allowed people to feel comfortable with being honest and speaking genuinely, without feeling the need to posture in a more formal manner.”

While SureSwift's unique position as a company with employees across fourteen time zones offers numerous advantages, it also means that despite having years of virtual collaboration, many of the leaders were meeting in person for the first time. With the establishment of the Summit Charter and encouragement from the corporate team to move away from traditional hierarchical approaches, the SaaS leaders felt enabled to quickly embrace a spirit of camaraderie and informality, strengthening personal bonds and encouraging more productive conversation over the three days.

Examining SureSwift’s updated Core Values

The first presentation of the Summit was an in-depth look at SureSwift’s new set of Core Values, a co-presentation led by Amanda McKay and James DeGreef. SureSwift’s growth and development over the past few years necessitated a revitalized set of company values to better reflect the company’s progression. The presentation allowed leadership to engage deeply with a topic they encounter daily, while also dedicating time to exploring how every company's values shape its culture. McKay and DeGreef detailed how it looks to actionably align with the Core Values in both day-to-day workflows and potential acquisitions. According to McKay, the shared response from SSC leadership felt enthusiastically synergistic,

“I had hoped for the presentation to be less of a lecture and more of an interactive group conversation with guiding questions, and that’s exactly what it turned out to be. All the leaders were highly engaged and passionate about their teams, culture, and how the Values are woven into the fabric of their operations. Bringing the presentation to life felt like a strong example of the Win-Together value put into practice.” 

The decision to start the Summit with a discussion of SureSwift’s Core Values was a prescient one, as the Values served as guiding principles for each presentation and exercise throughout the three-day event. Despite several leaders having faced a demanding travel day just hours earlier, Day One concluded with a sense of invigoration, excitement, and a collective eagerness to continue piecing together the growth puzzle as a global B2B SaaS company.

Day 2: Investigating SaaS pricing strategy, experimentation philosophy, and the SaaS superhero within

A packed Day Two began with a presentation from the LeadDyno team on their transformative pricing journey, offering the other portfolio businesses valuable insights into SaaS acquisition pricing strategies, including a value proposition showdown that challenged all the leaders to sharpen their approaches to value proposition alignment.

This was followed by an interactive presentation by Director of Operations Jac Stark, which focused on uncovering unique leadership strengths and finding the “SaaS superpower” within, helping individuals claim the expertise they bring to the table as a leader, both to their teams and to SureSwift. Stark took the group through solo and group work to discuss and parse out which skills and qualities set them apart as individuals and leaders.

“The catalyst for the session was honing in on the responsibility our leaders take to nurture and bring out the best in their teams,” Stark explains. “By completing the exercise on their own, they can then use what they've learned about the process to help their team members discover their strengths.” Stark highlighted the importance of receiving spirited endorsements from colleagues when it comes to one’s SaaS career, especially in a remote environment. Marketing Director Tracie Clayton agrees:

“I think sometimes there’s hesitation around claiming subject-matter expertise – a perception that someone might be arrogant or lack an appropriate amount of knowledge to be considered an SME,” explains Clayton, "The presentation required us to dig in and ask not only ourselves but also our peers, ‘where do I excel?’ And one surprising outcome of asking that question was  the collective discovery that qualities some perceived as negative were actually seen in a positive light by their peers.”

Stark‘s method of empowering the SSC leaders to uncover their Superpowers and adopt a shared language around the concept benefits each business from the top down. This methodology does more than enhance individual performance; it cultivates a cohesive and empowered leadership collective, capable of navigating complex challenges, driving organizational success, and inspiring others to collaborate across the product portfolio and alongside the corporate team.

Unraveling secrets behind the most successful SaaS businesses

The final presentation of the day was an exploration of SaaS experimentation strategy, led by Back in Stock Product Manager Dave Aidekman and John Austin, that encouraged the SaaS leaders to lean into the Stretch Core Value by embracing risk and change as an opportunity to learn and continually grow. When it came to choosing Summit presentation themes, Aidekman explained how the high-performing data behind strategic experimentation in SaaS made it a compelling topic of focus:

“Experimentation is such a powerful driver for growth. It's a key way to learn from customers, gather data to make decisions, and temper risk from significant changes. We all want to run more experiments, so it’s super helpful to share best practices while also learning from the occasional pitfalls our businesses have experienced.”

During his presentation, Aidekman outlined a series of successful experimentation strategies and frameworks used by renowned SaaS businesses, encouraging SureSwift’s SaaS leaders to draw from these tactics to build out the experimentation playbook within SureSwift’s Exceptional Operator Framework.

“There’s such a tremendous range of experience among the leaders – both in their current businesses and previous experience – that there were a ton of insights on what works,” Aidekman affirmed. “It's also not a one-size-fits-all topic, so we heard a variety of viewpoints and approaches tailored to diverse situations.”

While the presentations themselves helped lay the groundwork for further building upon SureSwift’s current strategies, the discussion that followed each presentation helped further the understanding and refinement of these methods, promoting deeper collaboration among the team.

Because the first day of the Summit was spent establishing foundational strategies for getting the most out of collaboration among the leaders, the second day allowed the SaaS leaders to more clearly define their goals and stretch targets for the year. Through intensive workshops and breakout sessions, the leaders were encouraged to thoroughly explore each portfolio business's specific challenges and opportunities, facilitating a shared vision and commitment to strong outcomes.

Day 3: Pursuing intentionality in marketing, communication, and future initiatives

On the third and final day of the Summit, Director of Marketing Tracie Clayton opened the day with a presentation on how brand marketing and performance marketing must play equal parts within a marketing strategy for a business to see optimized performance.

In the presentation, Clayton shared the reasons why it’s essential for businesses to utilize both marketing types: “Many people don't recognize that brand marketing is equally, if not more, important than performance marketing,” Clayton reveals. “You need to establish a trustworthy and relatable brand before you can sell people anything.”

Historically, 80% of marketing efforts emphasized brand promotion, while only 20% focused on direct sales, adhering to an 80/20 rule. With the onset of the digital age, the model inverted to 20/80, turning the majority of focus to performance marketing. Clayton cautions that a strategy of solely relying on performance marketing can diminish brand value over time by overemphasizing direct sales and underutilizing brand building.

“The challenge today is to integrate both approaches effectively,” Clayton explains. “Focus on identifying activities that you might not realize are already brand marketing. For instance, when someone lands on your website, that's brand marketing; how they got there is performance marketing.”

Clayton emphasizes the key role a company's website plays in the success of its marketing efforts. “What matters in particular is the first impression your organization makes and how it makes people feel, particularly in the digital space—it's all about how you relate to them through the language and images you use on your website.

Clayton’s marketing presentation was followed by an interactive workshop on effective leadership communication methods. Led by Amanda McKay and John Austin, this session challenged leaders to engage more intentionally in active listening through role-playing exercises. The workshop detailed scenarios highlighting common distractions in virtual meetings, such as zoom screens, typing, and phone use, which can make participants feel ignored.

McKay and Austin modeled how to respond empathetically and compassionately in these situations, emphasizing how important active listening is as a part of the Customer-Centric Core Value skill set. Not only does it assist with maintaining engagement within the business and avoiding the complacency that often accompanies frequent video conferencing, but it also helps to strengthen and solidify relationships with customers and investors.

To close out three days of productive collaboration and skill-building, Executive Chair Don Wharton joined the Summit remotely to deliver a poignant Vision Address on the future of SureSwift, where he highlighted the importance of SureSwift's commitment to integrity: "By focusing on transparency, SureSwift’s leadership is aligned with the interests of shareholders and investors, inspiring everyone at SureSwift Capital to continually strive for excellence." A question-and-answer session for the leaders followed this address, and Don closed with a thank you to the team, sharing that he was inspired and grateful for everyone's commitment to SureSwift's mission. This last session served as a commitment to the Core Value of Integrity and Accountability. It also helped tie each business’s day-to-day work back to customer-centric value and pulling the B2B global SaaS vision together.

After a jam-packed three days, the leaders returned to their responsibilities within each portfolio business, having completed a deep dive into bringing the Core Values to life in actionable ways within each level of day-to-day operations.

Concluding the SureSwift Summit: Constructing the puzzle pieces of the future

As the first of its kind, the 2024 SureSwift Capital Leadership Summit sought to bring the company’s Core Values to life by strengthening leadership bonds and bolstering communication and teamwork across the organization. The experience gave the SureSwift leaders the space and time to engage in meaningful discussions, share supportive insights, and build out strategies to carry SureSwift through 2024 and beyond.

Workshops and team-building exercises were employed to break down barriers, encourage open dialogue, and further build the lateral connection with the SSC corporate team. At the Summit's close, the attendees left feeling a stronger sense of connection to each other, to their SaaS careers, and to SureSwift’s vision for the future.

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