From Keep-the-Lights-On to the All-Hands Stage

The Challenge

Grasshopper had years of limited investment behind it. Engagement was declining, workflows were fragmented, and the product was missing capabilities customers now expected: no AI or intelligent assistance, and a mobile experience that sent users to the web for basic admin tasks. Yet it still served a distinct small-business segment and still produced real revenue.

Before 2022, Grasshopper ran as pure KTLO (keep the lights on): no new investment, and nobody talking about it. Under financial pressure, the company decided it was worth reinvesting in, to build new capabilities and slow its decline, and I was brought in to lead UX in November 2022. The team ran as a ticket-taker culture: product and engineering brought design in, but not research, so decisions were made without customer evidence.

Mandate: Bring a product the company had let slide back to life on a small team's budget, by finding out what customers actually needed instead of taking tickets.

My Role

• Partnered with the Director of Product and Director of Engineering on vision, strategy, and roadmap, and built trust with the VP of Product, who led the product overall
• Led UX strategy, aligning user needs with business goals and measurable outcomes
• Built the UX team (design, content, research), including key hires
• Owned UX staffing and resourcing against product priorities
• Defined UX success metrics (adoption, engagement, retention). Tableau covered usage at the account level (DAU/MAU, logins, calling, texting); task-level tracking came later
• Moved the team from ticket taking to evidence: staffed for existing trust, coached the designer to push back, and brought research and the Insiders program into the product

Approach

First, shift the culture: from tickets to evidence

• Get the right people in. I staffed the product with a staff designer who had done strong work for me before, and it worked well under the original product leadership. When product leadership changed, what the team needed changed with it, and in late 2023 I made a staffing change. I moved over a senior designer from Admin, chosen because she already had a strong working relationship with the Director of Product. She was ready for a new challenge, so the move worked well for both teams.
• Back the pushback. I met with her regularly so she could push back on requests with confidence instead of taking tickets.
• Bring research in. Product and engineering involved design but never research. In May 2024 I replaced our contract researcher with a full-time hire, a referral from people who had worked together before, and brought the team into the Insiders program so customers were in the loop.
• Build trust up and across. I didn't report to the VP of Product, but I built trust with him and helped him see where we could get the data we needed to decide what to build. I had already worked with the Director of Engineering on the call center work that later became AI Receptionist and AI Agent.

It was all about trust, and about pushing for more research, validation, and testing. The biggest single change was that research became part of how Grasshopper made decisions.

Discover: widen the problem before narrowing it

• Generative and evaluative research across small-business segments and industries
• End-to-end workflow mapping: call handling, admin, onboarding, routing
• A product audit across mobile and web to find fragmentation
• Usage data from Tableau: DAU/MAU, logins, and calling and texting volume
• Support tickets, customer feedback, and known pain points synthesized
• A competitive assessment against modern benchmarks (AI, automation, mobile-first)

Define: one problem statement

Grasshopper was a legacy small-business communications platform with declining engagement, fragmented workflows, and outdated capabilities, limiting its ability to drive sustained usage, retention, and revenue growth.

What we found:

• Fragmented core workflows: call handling, routing, and admin tasks were inefficient and disconnected
• Mobile that depended on the web: critical workflows required leaving the app
• Limited native support on iOS and Android, for users who run their business from a phone
• Inconsistent experience across user types: owners, operators, and solo users had different, unmet needs
• Low engagement: the product wasn't part of daily work
• Limited visibility and control, and missed automation opportunities

Personas

Persona	Who	In their words
Small business owner	Primary decision maker; professional services, real estate, legal, healthcare	"I need a simple way to look professional and never miss an opportunity."
Office manager	Day-to-day user; home services, retail, small agencies	"I need to keep calls and messages flowing without slowing down the business."
Solo entrepreneur	On the go; freelancers, gig workers, independent contractors	"I need to run my business from anywhere without juggling tools."

Solution directions

We chose to solve systemic workflow and engagement problems rather than add incremental features. The priorities were:

• Workflow simplification across core journeys
• A mobile-first admin and management experience
• Features that drive daily engagement
• An AI-assisted communication layer

Deliver and measure

The UX, Product, and Engineering trio delivered together. UX ran design QA through the build, and beta customers from the discovery cohort validated real-world use.

What shipped, all from my team's work:

• Spring 2025 launch: Unified Conversations (calls, texts, voicemails, and faxes in one thread per customer), conversation filters, global search, contact management, automatic call recording, and missed-call insights
• Mobile-first work: started under me, with many mobile-first features delivered before June 2025. The work continues, including the October 2025 launch.

Key Artifact

Results & Impact

• Business: Grasshopper went from keep-the-lights-on to beating its revenue and growth goals. It went from a product the company had let slide to one featured regularly in company all-hands meetings, and a very small team kept the run-rate investment low.
• Satisfaction: a 10–15% lift in NPS, CSAT, and OSAT, measured through UX surveys and corroborated by the Voice of Customer team's tracking.
• DAU and MAU grew, shared by the product's leader at multiple company all-hands (directional; figures not public).
• New features helped win new customers, attach rate grew, and call and text volume grew with it (directional).
• Growth unblocked budget: after I handed off, the work grew from a smaller body of work into a complete overhaul and gained a second designer. During KTLO it had none.
• Culture: research became part of how decisions were made, and design pushed back with evidence instead of taking tickets.

Reflection

What I'd do differently

Get ahead of leadership changes. When product leadership changed, I didn't recognize soon enough that the new style changed what the team needed from me. I gave a senior designer room to run because of his track record, when he needed closer support and more visibility for his work. Once I saw the issues I knew what to do; I just didn't dig in soon enough, and it led to a staffing change I believe could have been avoided. It's one of my biggest lessons as a leader: protect the team early, especially through a leadership transition.

Push for research a year earlier. It always comes back to research and validation up front. We could have pushed much harder, much earlier.

Instrument the tasks, not just the logins. Tableau gave us DAU/MAU, logins, and calling and texting volume, but nothing on the specific tasks users were trying to complete. We couldn't see the friction blocking user goals, or connect it to the business goals. Task-level tracking was in place by the time I left; I'd push for it from day one.