Core Values in Action: Dave Aidekman on SureSwift’s Data-Driven Approach

Data-Driven Decision Making at SureSwift Capital

In the fast-paced world of SaaS and technology, SureSwift Capital continues to push forward, with leaders like Dave Aidekman, the General Manager of Back in Stock, driving innovation. Our conversation with Dave explores his unique career journey, from national security to the dynamic tech and startup space. More than just a personal story, this discussion highlights one of SureSwift's Core Values—being Data Driven. As we dive deeper, you'll see how data, strategic insights, and diverse experiences are helping shape the future of SureSwift and its portfolio businesses.

Dave Aidekman’s Journey to Saas Leadership

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Can you tell me about your background before coming to SureSwift?

I have a very winding, unconventional path from national security to tech and startups, but I’ll give you an overview. I started my career working in government and national security policy in the White House, specifically in the White House budget office. I was looking at major defense acquisition programs, so I was doing a lot of analysis of technology, as well as strategic planning and financial planning around acquisition programs and the long-term global impact of those decisions.

I was in the White House on 9/11, and became part of the original Homeland Security Council team. I did that for almost seven years, then left government to do some consulting and strategy work around national policy, strategic planning, business development, quantitative and financial analysis, and technology. My partners and I did that for huge international companies, early stage technology startups, nonprofits, state and local governments – anyone who was looking for that type of advice.

That’s pretty impressive – how did you get from there to SaaS?

On the side, my wife and I turned our love of travel into a small business. We ended up building an online vacation travel business that we ran for eight years, focused on software and services to enable active group vacations. We ran that until 2020, and then started another small services business. At that point, I was interested in getting back into online and technology businesses, saw the opportunity with SureSwift and reached out.

Sounds like we’re lucky to have you. You clearly have a strong analytical background, can you speak to how you’ve translated those skills to SaaS leadership?

Absolutely. This is not novel, but one of the enormous opportunities with online businesses is how much data there is and how much you can understand about the behavior of your customers, their appetite and interests and needs. You can do it at a scale and a speed where you can gather meaningful amounts of data and analyze it quickly, experiment and iterate on changes that have an impact.

Throughout any of the roles I’ve been in, being smart and thoughtful about the data that you collect, how you interpret it, and how you use it is key. In SaaS, you’re using that data to understand the wishes of your customers, and you can be highly responsive to those wishes if you choose to be. It’s a huge opportunity, especially if you do it well compared to your competitors.

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Navigating the Intersection of Data Driven Decisions and Privacy Concerns

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How do you balance that with privacy concerns, especially with recent changes around data collection?

I think you have to do the best that you can with what is available to you. Accept that the data you gather may be incomplete, but that hopefully the data that you have is sufficiently representative of all of the users, and that what you’re learning is broadly applicable to all of the users.

Not everyone is going to want to opt in, so you have to just make sure that you’re delivering a more personalized experience for those who do opt in, and create value for them. It’s important to provide an experience for those who do share behavior and accept cookies that is augmented and improved because of that.

At SureSwift, Data Driven is one of our Core Values. Can you give me a rundown of what it actually means for a business to be Data Driven?

Foundationally, you want to be rigorously structured and organized in how you enact the data gathering and the metrics across your entire app and across the entire experience. You want it to be understandable to maintain and grow and adjust, so you want to have clear practices for how you set it up.

One example is having extensible naming conventions for your metrics, so that when you add to them and adjust them, they don’t overlap or conflict, and they’re understandable for all users now and in the future.

A second attribute of a strong foundation is to be very thoughtful and proactive about what your North Star metrics are, so that you can stay focused on what matters and not get bogged down and distracted by numbers and reports that don’t mean enough or change the behavior of the business. If you are unlikely to make a change based on the metrics you’re gathering, then they don’t add any value.

That’s something I’ve heard before, you should only track metrics that would drive a change in behavior.

It’s tricky. There’s a balance, right? You want to be thoughtful about what you can foresee using and what you can foresee making an impact on the flip side. You may not know in advance, and there’s some argument for collecting everything because you don’t want to decide twelve months from now that you wish you had been tracking something before. So it is a tricky balance.

Then you have to evaluate and strike a balance with what’s useful and how much time you have to spend on it. Looking at it, is this someone’s full-time job? Is this five people’s full-time job? Or is this someone’s one half-day a week job?

That has a big impact on your capacity to implement, track, and adjust with metrics. One way to balance it is to track a little more than you expect to use, but limit and filter what you’re reporting on to things that matter, being disciplined about not spending a lot of time on all the other things that you may find useful next year. It’s easy to consume your day looking at things that don’t matter.

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Core Principles around Saas Metrics: Measuring and Reporting

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Tell me what that reporting looks like on your team.

Sure. There are one or two ways to think about this, and one way is to think about the real North Star metrics, which are unsurprisingly typical around revenue, users, subscriber growth, and retention – the conventional SaaS metrics that you really want to understand and have visibility around. With that, we also make sure to look at our metrics rates of change that aren’t individual numbers, but how we’re doing over time and changing over time. My preference for metrics is more around rates than it is around individual static numbers.

The other way to think about this, and the other way we look at it, is to boil those metrics down to the focus things that individuals and teams impact. So, for example, we might have a metric around subscriber growth at that North Star level. Then we have a metric for our Customer Happiness team around upgraded users. So they’re not necessarily looking at the overall monthly revenue for the company, but a metric that they can have an impact on – satisfied customers who stay and upgrade. That rolls up to impact the retention, the revenue, the subscriber growth, the net dollar retention and other metrics that are at the overall business level. But individually, what they can impact day-to-day might be something different.

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Can you walk me through an example of data-driven decision making from your team?

One good example that we are working on now, and that we will always be working on, is the onboarding steps for users who install the free trial of our app. What we have done is create a very, very clear path from the beginning to the end of this process. We identify all the actions that the user will take from first exposure to the app all the way through install and trial, and through to becoming a paid customer.

In the analytics tools, we create an event for each discrete action that the user is supposed to take. This can be clicking a button, viewing a specific page, starting the form, finishing the form, submitting it, and approving the terms and conditions. Get the app installed in their Shopify store, do any types of activation behaviors like setup and customization. Then we look at all those steps the user goes through, and observe if there is any large or surprising drop off from one step to the next.

From there, we identify what we can possibly change or smooth in that stage. Maybe there’s an unnecessary step we can remove or friction that we can identify. Now, we can make adjustments and continue to measure to see the impact to see which steps have the biggest impact in obstructing or helping a user get through that funnel.

How are you measuring outcomes?

We’re measuring the overall conversion, in this case from viewing the app listing to installing the app. While we pay attention to the data around the step we adjusted, we really care about the overall conversion from beginning to end. We’ll see what the conversion rate before and after the change was, to see if we improved or degraded it with the action we took.

How long will you typically let a test like that run?

That will vary a lot on different statistical significance based on how big of a change is observed, and how many users. There are formulas that can evaluate that, but the short answer is if you see a very big impact, you can be confident with a smaller number of test users, and if you see a very small change, you need a lot more users to have confidence that it’s not random. For our app, it can be anywhere from two weeks to four weeks, depending on whether we see a very big change or small change.

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What’s next for Back in Stock?

We’re always listening to user feedback to figure out what is in demand, what our users want and need and what we can improve for them. We’re really guided both by what we hear from users, and back on the theme of metrics, we spend a lot of time validating what they tell us with what we actually see in the data. We’re going to continue looking at and upgrading the screens that our customers are spending the most time with, and regularly updating our understanding of what users want and making adjustments from there.

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Talking with Dave Aidekman, it’s clear that his diverse background—from national security to tech and startups—brings a fresh perspective to SureSwift Capital. His focus on data-driven decision-making aligns perfectly with our Core Values. Dave’s approach to using data to understand customer behavior and drive responsiveness shows the huge potential in online businesses. As SureSwift grows, having a strong focus on metrics and adaptability will be key to our success in the SaaS world.

Under Dave’s leadership, Back in Stock remains dedicated to listening to users and improving their experience. The attention to metrics—especially around customer satisfaction and retention—shows the team's commitment to ongoing improvement. By blending user feedback with data-driven strategies, Back in Stock is set to reach new heights and continue shaping SureSwift Capital’s portfolio.

If our dedication to growth and innovation resonates with you, check out our Careers Page to see how you can join the SureSwift team.