Smartsheet: Scaling Autonomy in the Enterprise Customer Success Function

This blog post is part of 80+ case studies of progressive organizations we created for the ZeroDX awards 2025. These organizations embody the principles of RenDanHeYi in their work structures:

• Zero Distance to customer: Decision what to build is based on insights from the marketplace

• Autonomy: Small teams with full decision-making autonomy enable speed in execution

• Shared Rewards: Everyone in the micro-enterprise participates in its financial success.

As the team responsible for ensuring large enterprise clients renew and expand their platform use, Customer Successwas not just a support function; it was critical to sustaining Smartsheet’s long-term growth.

"I decided to treat it as a leadership experiment in self-management," Chris explained. Inspired by Humanocracy, Corporate Rebels, and RenDanHeYi, he launched a playbook grounded in trust, transparency, and distributed decision-making. For Chris, this wasn’t just an operational fix. It was a philosophical choice: to test whether the principles of autonomy and mutual accountability could outperform control in a high-stakes, high-revenue environment. The principles behind this transformation echoed core RenDanHeYi values: decentralization of authority, zero distance to the user, and dynamic evolution of internal structures.

One of the first steps was to disable prescriptive software systems that dictated daily tasks. Team members were empowered to decide how best to serve the customer. "We had some formal systems that were supposed to tell theteam what they were supposed to do in terms of work. We turned that off. I didn't want a computer telling you what to do because I'm not confident that the guidance it's giving you works." The outdated system, designed to enforce alignment from above, often made worse decisions than the humans closest to the customer.

In contrast, AI was embraced as a tool to enhance clarity and alignment. Chris and his team used generative AI to help map customer adoption roles and clarify what services could be offered. This work directly informed arestructuring of team responsibilities and a renewed focus on value delivery. By surfacing hidden complexities in the team's workflow and customer interactions, the framework helped clarify roles and needs that had previously been difficult to coordinate. The generative AI outputs supported more effective prioritisation and highlighted the customer adoption roles that mattered most.

Among the structural outcomes was a new RACI for renewals. Short for Responsible, Accountable, Consulted,and Informed, a RACI matrix defines clear roles in processes or decisions. In this case, it centred customersuccess efforts on value realization and made responsibilities visible across teams.

Changes to the formal systems, however, were not immediately possible. Employees were trusted to make decisions,but approvals still had to be executed within rigid structures. "If you wanted to extend a deal for two to four weeks, adeal over a certain size requires an executive to formally approve it in the system," Chris said. Although team members were now driving conversations and making frontline decisions, the formal systems still required executive approval. Chris would step in to complete the process, reinforcing their choices rather than overruling them. "I'm going to trust your decision," he told them, signaling a shift in leadership from directive to supportive.

As autonomy expanded, so did the need for mindset shifts. Many employees had never been asked to assessaccount health or make renewal decisions. "There was a type of employee that thought 'I've never had to make that decision before'. Until people saw that I was true to my word regarding trust and self-management, there was still this sort of weird, grey time."

Over time, team members didn’t just become more autonomous, they became more connected. Visibility into each other’s decisions created a culture of peer accountability. People started learning from one another, not just from above.

The team launched a major customer-facing initiative to anchor decision-making in business outcomes: co-creating over 300 outcome stories. These narratives, developed with solution owners inside client organizations, captured realadoption journeys and tangible results. "We started out by targeting three per account. We'd go to the person that built it or the senior person in it that owns it and talk to them about what it is, why they built it, and what kind of value."

The impact of these stories was multifaceted. Internally, they shifted the team's perspective from resolving technical issues to driving measurable business outcomes. Chris captured this shift clearly: "Because if you're talking in the terms of, 'Hey, did you know that you supported double the revenue with half the staff and you did it through our technology?' that's a fundamentally different question than 'Did you configure your dashboard the right way?'" By reframing the conversation around value rather than functionality, the team deepened its understanding of its role, not just as technical support, but as a partner in the customer’s success.

The stories gave team members a direct line to the real impact their work was having, making it easier to prioritize, advocate, and innovate with confidence. Externally, the stories empowered customers to advocate internally andunlocked expansion opportunities. They also made visible a reality previously hidden from Smartsheet leadership: that 85% of the work being done in the platform occurred below the senior director level. This reinforced a key RenDanHeYi idea: value creation happens closest to the front line, and systems must be designed to recognize and support that.

The team’s performance led to wider structural change. Within six months, the experiment scaled to a 200-personorganisation managing $1.2B in renewals. Team leads gained a formal voice in strategy. A Retention SOP wasintroduced to clarify decision rights between Sales and Customer Success, and internal transparency tools helped benchmark account performance across peers. Compensation was also tied directly to retention outcomes.

Smartsheet’s transition to private equity ownership gave the transformation further momentum by allowing more flexibility to experiment with decentralized practices. While public company structures can support autonomy, the move to private ownership helped accelerate decision-making at the edges by reducing internal hesitation around perceived business risk. It underscored that structural innovation is possible in any context. What matters most is leadership commitment and a willingness to trust teams to lead.

As Chris reflected, "We're only scratching the surface, but even a partial experiment showed us what’s possible."

What began as a crisis response has become a bold reimagining of how work, leadership, and value creation can be organized in a large enterprise, true to the spirit of RenDanHeYi, yet adapted to the constraints and opportunities of Smartsheet’s evolving context. It is a live demonstration that structural innovation doesn’t always require a full organizational overhaul. Sometimes, it starts with one leader choosing to trust their team.