saas.unbound is a podcast for and about founders who are working on scaling inspiring products that people love, brought to you by, a serial acquirer of B2B SaaS companies.

In episode #27, Anna Nadeina talks with James, CEO, and co-founder of GoSquared, a real-time analytics platform, and also currently building EcoSend, an email marketing platform for climate-conscious businesses.

The Early Days of GoSquared

In the ever-evolving world of SaaS, few companies can boast the kind of long-term success and sustainability that GoSquared has achieved. Founded by James Gill and his co-founders back in 2005, GoSquared has weathered the storms of industry changes, economic fluctuations, and the ever-shifting tides of consumer preferences to emerge as a true powerhouse in the real-time analytics space.

From humble beginnings as a side project, GoSquared has grown into a thriving business that continues to innovate and adapt to the needs of its customers. In the early days, James and his team were driven by a passion for creating tools that could help businesses better understand and engage with their audiences. With a keen eye for detail and a relentless pursuit of excellence, they set out to build a platform that would revolutionize the way companies approached their online presence.


Challenges and Surprises Over 18 Years

As with any successful venture, GoSquared’s journey has been marked by both triumphs and challenges. James openly acknowledges the surprises and obstacles the company has faced over the past 18 years, noting that the SaaS landscape is constantly evolving, and staying ahead of the curve requires an adaptable mindset.

One of the key challenges Gill and his team have navigated is the need to continuously evolve their product offerings to meet the changing needs of their customers. “The market is always shifting, and what worked for us five or ten years ago may not be as relevant today,” Gill explains. “We’ve had to be proactive in identifying new trends and opportunities, and then quickly adapting our solutions to stay ahead of the competition.”

Another significant hurdle has been the need to maintain a strong focus on user success and retention, even as the company has grown and scaled. “It’s easy to get caught up in the metrics and lose sight of the individual customer experience,” James says. “But we’ve always believed that if we can truly understand and support our users, the rest will follow.”


The Importance of Cohort-Based Analysis in User Success

One of the key strategies GoSquared has employed to ensure long-term user success is the use of cohort-based analysis. By closely tracking the behavior and engagement of different user cohorts over time, the team has been able to identify patterns and trends that inform their product development and customer success efforts.

This focus on user-centric insights has been a hallmark of GoSquared’s approach, and it’s a strategy that James believes is essential for any SaaS company looking to build a sustainable and loyal customer base.


The Evolution of Customer Acquisition Strategy

As GoSquared has grown and evolved, so too has its approach to customer acquisition. In the early days, the team relied heavily on content marketing and SEO to drive awareness and attract new users. But as the market became more crowded and competitive, they had to adapt their tactics to stay ahead.

“We’ve always believed in the power of organic growth, but we’ve also recognized the need to diversify our acquisition channels,” James says. “Over the years, we’ve experimented with everything from paid advertising to strategic partnerships, always with an eye towards finding the most effective and sustainable ways to reach our target audience.”

One of the key insights James and his team have gleaned is the importance of aligning their acquisition efforts with the overall customer journey. 


The Birth of EcoSend: A Climate-Conscious Email Marketing Solution

While GoSquared has been the primary focus for the past 18 years, James and his team have also been exploring new opportunities in the SaaS space. One of their latest ventures is EcoSend, a climate-conscious email marketing platform that aims to help businesses reduce their environmental impact.

The development of EcoSend has been a labor of love for James and his team, and they’ve approached it with the same level of diligence and attention to detail that has made GoSquared so successful.


Customer Insights and Product Management Challenges

As James and his team have navigated the development of both GoSquared and EcoSend, they’ve faced a number of product management challenges, particularly when it comes to gathering and acting on customer insights.

“One of the biggest hurdles we’ve had to overcome is the sheer volume of data and feedback we receive from our users,” Gill explains. “It can be overwhelming to sort through it all and identify the truly meaningful insights that should inform our product roadmap.”

To address this challenge, the GoSquared and EcoSend teams have implemented a rigorous system of customer research, user testing, and data analysis. They’re constantly gathering feedback from their users, both through formal channels like surveys and interviews, as well as more informal touchpoints like support interactions and community discussions.


Navigating Multiple Products and Business Impact

As GoSquared and EcoSend have grown and evolved, Gill and his team have had to navigate the unique challenges of managing multiple product lines and ensuring that each one is having a meaningful impact on the business.

To achieve this balance, James and his team have implemented a rigorous system of performance tracking and cross-functional collaboration. They closely monitor the key metrics and KPIs for each product, and they regularly convene to discuss strategy, identify opportunities for synergy, and make data-driven decisions about where to focus their efforts.

“At the end of the day, our goal is to create products that truly make a difference for our customers,” James says. 


The Biggest Win, Failure, and Time Management Hack

As James reflects on his 18 years of leading GoSquared, he cites the company’s ability to maintain its focus and vision as its biggest win. “It would have been easy to get distracted by the shiny new trends or the temptation to chase after every new opportunity,” he says. “But we’ve always stayed true to our core mission of helping businesses understand and engage with their audiences.”

One of the time management hacks that Gill has found particularly helpful is the practice of “deep work.” By carving out dedicated blocks of time to focus on high-impact tasks without distractions, he’s been able to boost his productivity and maintain a sense of balance in his work-life integration.

“It’s so easy to get caught up in the constant stream of emails, meetings, and notifications,” James says. “But when I’m able to really immerse myself in a project or problem, that’s when I’m able to do my best and most impactful work. It’s a practice that has served me well over the years, and one that I’d recommend to any SaaS founder or leader.”

Head of Growth,