Categories: Sales Leadership | Artificial Intelligence
Great sales leaders know how to make the number, but the ability to do that consistently requires more than just great sales skills. The best revenue leaders understand the critical need to equip individuals with the proper tools for revenue success and drive organizational outcomes. A great sales leader understands the importance of a structured sales discipline while reinforcing methodologies that drive measurable results. Veteran Sales Leader and Current Shopify Chief Revenue Officer Bobby Morrison recently joined the Revenue Builders podcast with John Kaplan and John McMahon to talk through his lessons learned and his blueprint for great sales leadership. Morrison knows how to grow and scale companies; from his sales leadership roles at Verizon, where his leadership helped drive $8.3B in revenue, and at Microsoft, where his segment increased revenue from $15B to $25B. Now, at Shopify, he’s led their shift upmarket to an aggressive 30% revenue growth rate in Q1 of this year.
Morrison is maniacally focused on execution, ensuring his teams are customer-centric and embracing AI-first strategies. His Revenue Builders podcast interview is packed with great tips from Morrison, McMahon and Kaplan on critical components to active leadership. Here are some key takeaways.
The Fundamentals of Active Leadership
A company thrives with leaders who lead from the front, coach, set goals, and are a driving engine for growth. They don’t sit back and cross their fingers that their teams will execute. They don’t complain about the outcome. They don’t preach the “what”. They provide the how and articulate the why. The best companies have leaders who embrace this type of active leadership. When companies use leadership as the central engine for revenue growth, sales managers are required to do more than just oversee teams and assist in deals. They’re embedded in the business, driving revenue, ensuring customer success around net retained revenue and growth, and truly understanding customer needs and preferences.
Strong leaders deliver on the forecast. They ensure higher win rates among their teams because they consistently enable their teams to execute and close deals. They can understand the market dynamics, anticipate challenges, and strategically help their teams position solutions that align to customers' needs and desired business outcomes. As Morrison puts it, “Managers should always be your best closers because they should have the best technical depth and should always be a step ahead of whatever you have across your business.” Successful sales leaders don’t abdicate their responsibility for the number. They own it. They’re hands-on, ensuring a smooth alignment between market trends, customer needs, product offerings and sales execution. When done correctly, they drive sustainable revenue growth regardless of any market fluctuations.
The Role of Sales Leadership in Driving Customer & Team Success
Great sales leaders are always aware of the influence they have on not just the deals they negotiate, but also their customers and team. They must build a supportive environment where customers achieve their outcomes and team members thrive. “Strong leaders prioritize seamless customer experience by anticipating future challenges, having a deep understanding of their needs, along with driving innovation that enhances satisfaction.” Great sales leaders know how their solution delivers customer value, and they know the buyer behaviors that align to that value. When done correctly, they can refine engagement strategies and understand their customers more deeply while helping other team members do the same. This understanding also enables them to anticipate customer challenges before they arise, allowing for a smoother sales process. Perhaps the most critical skill of a great sales leader is to ensure their teams have the proper tools and coaching consistently, so they can excel.
For Shopify, that meant shifting their organizational structure. Morrison’s teams work in a pod-like structure that ensures cross-functional alignment and customer success. Their pods are industry-specific and help push customer focus between solution engineers, partners, development, managers and sales, etc. From solution engineers to account executives, the pod structure creates stronger customer continuity and internal efficiency.
Shifting Leadership Training to Real-World Scenarios
Many leadership programs rehearse the same theoretical exercises that fail to reflect the conditions of a true market. They sound good in a training room, but when it comes to practical application, they fall flat. Managers are left to squander when they’re faced with the twists and turns of real-life scenarios. Instead, a great sales leader emphasizes practical learning and adaptability by helping teams apply best practices to live deals and customer conversations. They demonstrate. They enable and they coach effectively. Consistent training aligned to real-life scenarios has been a success at Shopify. Morrison’s teams infuse any new content with existing content in their training. This “draft in” approach ensures managers build new concepts on existing best practices, increasing their ability to adapt to any situation thrown at them in the market. This learning focus enables their customer teams to be more efficient at problem-solving and meeting ever-evolving customer expectations.
Integrating AI into Sales Training
Shopify made news earlier this year after their CEO’s AI-First Memo was released. The use of AI is mandatory at Shopify, and Morrison is ensuring its also helping his teams execute.
Morrison says leaders need to go beyond simply adopting AI; they must actively train their teams to harness AI’s full capabilities. Traditional training materials rely on outdated and hypothetical scenarios that often fail to demonstrate AI’s role in modern commerce. By embedding AI into leadership development, Shopify ensures its managers understand how the company’s AI tools can help them drive the outcomes they need internally and externally with customers. Morrison’s approach exemplifies how AI-first thinking drives more than just internal efficiency but also creates stronger alignment between the ever-changing market dynamics and sales execution.
Embrace Next-Level Leadership
Strong sales leadership is more than just managing quotas and hitting targets. It also requires fostering alignment, driving revenue, and adapting to technological shifts. The next big rock for every company leader right now is effectively and productively embedding AI into the go-to-market motion. We brought together three experts in the world of AI and sales for an action-oriented discussion on what leaders should be doing now: winning strategies, strategic customization, and the biggest mistakes to avoid. Watch the panel discussion on AI in Leadership to start building a strategy that makes AI a strategic growth multiplier for your teams.
