How testimonial tree is scaling their business with a virtual team
Virtual Success Show
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Episode breakdown
In this episode, special guest and founder of testimonial tree, jason dolle, shares with us how he is scaling his business with the help of a virtual team. Jason, who has an engineering background, started the testimonial tree to convert customer feedback and experiences into powerful tools that can help business owners grow their business, and in the process has grown a successful business of his own.
- More about Testimonial Tree
- How Jason has grown his company by bringing the right people onboard at the right time
- The ways in which Jason communicates with his virtual team to keep everyone on a path for success
- The importance of planning now, for the future
The culture fit piece is something that’s really hard to get right. But it’s so pivotal to actually having a successful team. It’s worth investing time in that.
In this episode
00:00 - Introduction
Barbara interviews Jason Dolle, founder of Testimonial Tree—a SaaS platform for collecting testimonials. Originally an engineer turned luxury real estate agent, Jason was inspired to create the tool after a $4.4M sale. Now, the company generates millions in annual recurring revenue, serves 95,000 customers, and maintains a 95% retention rate. Jason discusses growing a SaaS business and team.
01:49 – What is Testimonial Tree?
Jason created a tool in 2013 to collect client testimonials for social media, especially in areas he couldn’t market directly. It evolved into a business after a real estate broker saw its potential. Now, it automates customer feedback for marketing, learning, and HR, helping companies grow through improved customer experience. Like Barbara, Jason calls it an “accidental business.”
03:26 – The power of stories
Barbara highlights the power of testimonials and storytelling in marketing, noting how difficult it can be to collect them effectively without a solid process or tool like Testimonial Tree. She admits her team misses opportunities. Transitioning the conversation, she praises Jason’s company structure—his team works in-office while he operates virtually—and asks about how his team began and early challenges.
Barbara expresses optimism for the outsourcing industry, expecting remote work and AI adoption to continue rising. She sees offshore staffing as a no-brainer, especially as businesses seek cost-saving strategies during economic downturns.
04:34 – How Testimonial Tree started out
Jason started his business solo, building everything himself part-time. As things grew, he brought on a local contractor—an old friend—for help. Initially delegating small tasks, he gradually built trust and offloaded more work. However, when growth demanded more commitment, the contractor chose to stay in his stable, high-paying job, highlighting the challenge of hiring top talent without matching compensation or risk tolerance.
06:55 – Funding helped grow the business
In 2016, they raised $1.25M, which enabled the company to grow beyond a minimal team. The funding accelerated expansion into new verticals like healthcare and insurance. Jason, with an engineering background, had no prior leadership experience and found the transition to leading a team challenging. He continues learning, reflecting on early mistakes and the importance of hiring the right people.
09:00 – Finding the right people…
Jason initially chose a cheaper hire over a more experienced CTO to stretch the budget, but the decision backfired. The hire underperformed and lacked commitment, leading to Jason’s first painful firing. He admitted his interview process was weak and overly trusting. The experience taught him the importance of thorough vetting, culture fit, and building better hiring processes for future success.
11:49 – How do you run the company today?
Jason is often on the road pursuing major deals, so staying connected with his mostly in-office team is key. He relies on tools like Slack and strong internal leadership to maintain control. Regular check-ins with a trusted team member help him stay aware of company issues. His goal is to lead without micromanaging, though he’s still refining that balance.
13:12 – What is your communications plan?
Jason’s team uses Slack as the main communication tool, supplemented by Monday morning stand-ups and Friday wrap-ups to review progress, challenges, and celebrate wins. They also use tools like GitHub, Zendesk, Basecamp, and Atlassian for project and ticket management. Jason values these meetings for fostering creativity and team cohesion, and plans to join virtually while expanding with offshore team members to maintain culture and connection.
18:54 – Have you had offshore staff?
Jason’s first experience with offshore staff was a contractor in Pakistan for a mobile design project. Communication was mainly through Slack, relying on visual mockups and annotations. Despite some payment challenges, the collaboration went smoothly and proved effective for specialized, project-based work. Jason sees value in using offshore expertise for specific needs.
20:25 – Tips for building a SaaS company
Jason advises that scaling from initial revenue to rapid growth requires building scalable processes across all areas—onboarding, customer service, and sales. He encourages his team to think beyond their current roles, planning for future growth and efficiency. Rather than one-off fixes, creating repeatable solutions, like knowledge articles, helps reduce bottlenecks and supports sustainable scaling in a fast-growing SaaS business.
22:29 – Plan now for the future
Barbara emphasizes the importance of building processes with future growth in mind—designing systems to handle five times the current volume to avoid breakdowns during scaling. Jason agrees, highlighting the challenge of transitioning from doing every job yourself to training others, while maintaining what makes your service unique. They also agree that training offshore or local hires is necessary since every company has its own way of working.
25:35 – How long does it take to integrate a new recruit?
Jason and Barbara agree that even experienced hires need about two to three months to fully onboard. While core skills come quickly, mastering customized, nuanced work takes longer. They emphasize setting realistic expectations and viewing onboarding as a long-term investment, whether hires are local or remote, allowing new team members to adapt culturally and develop their own style.
27:48 – Invest in your people
Jason and Barbara emphasize investing time and energy in hiring motivated, enthusiastic people—especially support assistants—with the right mindset over skills, which can be taught. They focus on building scalable teams and systems for long-term growth, using support assistants to support in-house staff, delegate tasks, and develop leadership, while accepting mistakes as part of learning and growth.
30:43 – How do I use support assistants?
Barbara explains that when scaling a company, businesses can either hire more local staff or offload routine tasks to support assistants or offshore teams. This approach lets onshore employees focus on higher-value, strategic roles. It’s a cost-effective way to grow while leveraging support roles efficiently. She also plugs Testimonial Tree as a tool to boost client feedback and testimonials.
31:48 – Learn more about Testimonial Tree
Jason explains that TestimonialTree.com offers demos and helps businesses leverage customer testimonials not just for marketing but to understand what truly “wows” customers. They use data to improve company performance. Support assistants help manage and analyze this data, freeing leaders to focus elsewhere. The platform values customer feedback for growth, maintaining close relationships, and plans to use support assistants to enhance user support and scalability.
36:04 – Wrapping things up
Barbara thanks Jason for sharing insights on teams, systems, and scaling businesses using onshore or offshore support. She encourages listeners to visit TestimonialTree.com and shares her positive impression of the platform. She asks the audience to leave a rating and review on iTunes to help spread the message, ending the podcast on a friendly note.
