Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!
Our guest for Episode 61 is Andrew Dubowec, Chief Growth Officer at League. Before joining League in 2016, Andrew held leadership roles at Union Capital and North. He brings more than 15 years of experience to the conversation.
In this episode, Ross and Andrew discuss how to promote an “own it” culture, embrace growth as a team sport, and build a culture of transparency.
Listen to the episode here, and get the key takeaways from our conversation below.
Promote an “own it” culture
Andrew’s first piece of advice for those striving for execution excellence in sales is to cultivate an “own it, we trust you” culture. The idea is to empower sellers — regardless of their experience level — to venture out and try new things. Whether that means exploring new verticals, entering untapped geographies, forming new partnerships, or experimenting with fresh strategies.
The outcome is simple, yet transformative: when sellers feel trusted to take initiative and make decisions, they are more likely to think outside the box and drive impactful results. “Having a strongly held conviction, but willing to be wrong, is an important part of leadership,” Andrew explains. This mindset creates a work environment where risk-taking paves the way for innovation and continuous improvement.
Andrew believes that, when viewed in isolation, some experiments might appear risky or unconventional. However, “when you actually zoom out, you often realize these experiments contribute to significant learning and are aligned with the company's long-term goals.”
Embrace growth as a team sport
When it comes to building a successful sales organization, growth is a team sport. It requires a blend of internal and external stakeholders working toward a common goal. "The nexus of our selling unit isn't just the Account Executive," explains Andrew. "It encompasses many different functions around that person, from solution engineering to product, technology, and professional services. This means we have to be intentional about how we bring that team together, while also educating those in non-sales roles on how to engage in the sales process effectively."
At League, embracing growth as a team sport means integrating their internal processes with transparency. Andrew’s team uses Slack to communicate relevant information so that everyone involved in the sales process is well-informed and equipped to support the customer throughout the buying journey and beyond.
"We're very intentional about preparation," Andrew continues. "We make sure our team members are aligned on our strategies to win. To empower our customers effectively, we dig into their specific problems, buying environments, and business cases. This raises an important question for us as leaders: 'How can we institutionalize these insights better through our training and discovery phases, and design a unique buying experience for the customer?'"
Andrew also advises leaders to define what great looks like at every stage of the customer journey. Doing this helps establish success criteria throughout the process so teams can align their efforts with strategic goals, enhance customer interactions, and drive organizational growth.
Build a culture of transparency
Building a culture of transparency isn’t just about sharing information — it’s about cultivating an environment that welcomes and values feedback and diverse perspectives. The objective here isn’t to play “nice,” it’s to get the answers right and make the best decisions for the customer.
“Customers aren’t just buying your solution. They’re buying you as a partner,” says Andrew. “If you think about selling to and partnering with a senior C-suite executive, they want a point of view, yes — but they also want agency in the decision making. Sometimes, what they’re missing is a well-structured choice. So your job is to help them make better decisions, and some of that happens by giving them agency and control, which in turn builds advocacy for your solution.”
Andrew notes that sales reps, who are often highly extroverted, might struggle with self-criticism and hesitate to express constructive criticism. This tendency can hinder the development of a transparent and mutually beneficial relationship with clients. Addressing this requires both data and intuition, this way the “system” and “data” can work together to reinforce the cultural value of transparency.
About Andrew
Andrew is the Chief Growth Officer at League, a growth-stage infrastructure software platform enhancing digital consumer experiences in healthcare, where he leads GTM strategy and revenue operations. In 2019, he co-founded Union, an early-stage venture capital fund uniting over 100 entrepreneurs, operators, and investors to support founders in building their companies.
