Driving the vision and execution of moving Flex from a customer support market to customer experience.

Context

Flex is a programmable contact center solution.

Problem

Flex was struggling to grow in the customer service market segment.

Two years after its launch, Flex struggled to gain traction in the saturated customer service market, especially in the enterprise segment, where it faced strong competition from feature-rich solutions. Twilio also lacked an enterprise GTM strategy, while product teams grappled with reliability issues and feature gaps, without a clear growth plan for Flex.

At the time, Twilio had no defined software strategy, relying heavily on its low-margin API business for revenue. There was an urgent need to develop a software-focused strategy to improve overall margins.

Approach

Build a vision & execution plan to pivot Flex from customer service to customer engagement.

Through customer interactions, we discovered that some were using Flex as a customer engagement solution, extending it for outbound sales communication. This was a game-changer—if Flex could support sales needs, we could pivot into the customer engagement market, expanding our addressable market from $20B to $150B. Additionally, this shift would allow us to target profit centers instead of cost centers and accelerate SMB growth.

Recognizing the opportunity, I partnered with the business unit head, PM and Engineering leaders to drive this initiative forward by:

Building a product vision

Defining the problem and solution space

Driving execution for customer engagement

Shifting focus to customer's customer experience to build a compelling vision.

To move forward, we needed C-suite buy-in and potential investment. We focused on crafting a compelling vision while simultaneously defining the key value that the customers are looking for in a customer engagement tool. Rather than centering solely on businesses, I pushed to understand consumer needs, enabling brands to deliver a best-in-class experience.

Our research revealed a key pain point—brands lack memory, forcing consumers to repeat themselves. In response, we designed a proactive sales experience that retained customer context throughout the engagement cycle.

Using these insights, we defined core value propositions for each persona:

Consumers: A multi-channel experience that retains context across interactions.
Representatives: Access to consumer context and engagement history for better service.
Managers: Visibility into customer satisfaction and intelligent call routing.

Translating vision to consumer-centric product requirements.

Although we didn’t secure immediate funding, we reprioritized the Flex roadmap to form a lean tiger team for this initiative. We focused on defining a Most Lovable Product (MLP) for the SMB market, and I established a continuous feedback loop with both existing and potential customers to ensure we built a solution that truly addressed their needs.

Our research showed a shift away from traditional support metrics (MTTR) toward customer satisfaction, especially among newer businesses. Companies prioritized delivering a superior experience over simply reducing support costs. Consumers, in turn, sought engagement continuity, a single brand contact, and control over interactions.

Using these insights, we prioritized features around three pillars:
Empower consumers with control over engagements.
Foster empathy in sales agents.
Enhance operational efficiency.

To address time-to-market and effort concerns, I collaborated with the leadership team to launch a mobile-first versionwith limited functionality, introduced as a separate product line called Frontline.

Defining a common executional framework to drive multiple initiatives in parallel.

As we gained traction on the Flex vision and began executing the mobile experience, we aimed to align initiatives to minimize rework when Flex Web transitioned to customer engagement.

During this time, we scaled UX from 5 to 15 people, balancing efforts between the Flex vision and the next release. I structured the team around key areas, established UX leadership, and worked with leadership to align roadmaps and strategy reviews.

To foster collaboration, we introduced cross-team crit-pods and design sprints, along with regular readouts and reviews to ensure seamless execution across teams.

Outcomes