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Turning "why this approach?" into product strategy

I stopped designing what was asked for and started asking why - that question eventually became the company's core product.

Company
Boomerang (formerly BuyerAssist)
Role
Product Strategist / Head of Design
Team
20 (incl. Founder, CTO, CRO)
Business Context

A 20-person team, moving fast without pausing for clarity.

Boomerang's founders, including the CTO and CRO, were racing to ship under real investor pressure to show momentum fast. What got built worked as individual pieces, but none of it connected into a system a rep could actually rely on.

The Problem

Nobody was asking why before building.

Every customer call produced a new feature idea, and the backlog grew faster than the team could ship or measure any of it. I flagged the core problem early, but there was no room for that conversation yet - Mutual Success Plan shipped anyway, and it failed. That's when the real question showed up: what do we do next. Three months of silence and roadmap thinking followed before Warm Referral came out of it.

Constraints
Small team, no room for building the wrong thing twice
Founders under investor pressure to show momentum fast
No dedicated product strategist - the gap I ended up filling
My Leadership Role

I initiated it, and owned the whole workflow.

Warm Referral wasn't handed to me - it came out of the three months of ideation after the pivot. I spent that time going through hundreds of sales tools to understand how they positioned themselves and where the real gaps in the market were, and going back to an influencer map I'd built as part of Mutual Success Plan - org structure, and the individual influencers sitting inside a buying team.

That map became the base I kept building on: I started asking what other data we could surface to a rep beyond it, and the Chrome extension idea came directly out of that question. The proposal that landed was simple - surface the data inside the workflow a rep already lived in, instead of asking them to adopt something new. That's the idea that changed the direction of the company.

I owned the complete workflow end to end from there: how a lead gets understood the moment it lands in the CRM, how a warm path gets surfaced, and how the ask actually gets sent. That meant working directly with the founder, CTO, and CRO on product direction, not just screens - it became the new roadmap.

Leadership Scope
Cross-functional collaboration
Partnered directly with the Founder, CTO, and CRO on product direction and roadmap
Led a team of 3 designers executing the workflow end to end
Worked with engineering to combine Salesforce, LinkedIn, and a Chrome extension into one system
Validated the product directly with partners, with the CEO in the room
Mentored a junior designer through the build
Critical Product Decisions
01
The Chrome extension bet
A show-stopper bet - if reps wouldn't adopt something living inside the tools they already used, the concept died with it. It worked, and became the moment that took Warm Referral from an internal idea to the company's next stage.
02
Pivoting away from Mutual Success Plan
Their first big bet wasn't working. I pushed a different idea instead.
03
Warm Referral: surfacing trusted paths from CRM data
Instead of cold outreach, surface the warmest route into an account using relationship data already sitting in the CRM. This one worked in market.
Execution

Since the workflow was mine to build, I created it end to end and validated it directly with partners, with the CEO in the room. My own team was three designers who'd been split across the website and marketing workstream - we were small enough that working with engineering, marketing, and product wasn't a separate ritual, it was just how the day went. Three months of design and partner validation later, we had our first customers.

The system is fully automated once a rep connects their CRM. When a new lead lands in Salesforce, Warm Referral reads it, cross-references the account's org chart and each stakeholder's work history, and surfaces the warmest path in - through a Chrome extension that overlays directly on Salesforce or LinkedIn.

A rep picks a path, and the system drafts and sends the referral ask by email or Slack. Once the connector responds, the referral gets added straight into the rep's lead list. None of these tools were built to talk to each other, so getting Salesforce, LinkedIn, and a Chrome extension to work as one continuous workflow meant chaining automations across all three - a pattern I leaned on from automation work I'd done earlier at Zoho.

Mutual Success Plan Pivoted away
Chrome extension for reps Shipped → revenue
Warm Referral engine Now core product
Evidence
account scoring
Accounts dashboard showing ICP grade, overall score, and referral count per account
Every target account scored and ranked automatically - ICP grade, overall score, referral count, all computed.
account detail · contacts
Account detail view - every contact scored with decision level and referral strength
Drill into any account and every contact is scored the same way - decision level, referral strength, location, all pulled automatically.
org chart · pulled automatically
Automatically generated org chart for a target account
Full org chart per account, pulled automatically once the CRM is connected - no manual mapping.
chrome extension · linkedin overlay
Chrome extension overlaying account intelligence directly on LinkedIn
The same account intelligence follows reps onto LinkedIn - Boomerangs and Customer Advocates surfaced without leaving the page.
account 360 · referral relationships
Account 360 view showing referral relationships surfaced on LinkedIn
The moment a lead lands, the system surfaces who's already connected - tagged for ICP fit, recently hired, and past buyers.
the automated ask
Automated referral request email with a one-click accept action
One click drafts and sends the referral request - the connector just has to say yes.
slack digest
Slack bot delivering a daily digest of warm referral paths
Reps get warm paths delivered daily in Slack - no need to open the CRM to find one.
Outcome
60%
less manual research time per rep
35%
higher outreach success via warm paths
2.5 wks
shorter average account penetration

These numbers came from Mixpanel, which tracked rep activity through the rollout, not an estimate. The Chrome extension is what took Warm Referral to Armis, a $300M-ARR cybersecurity company - that's where Boomerang's enterprise story actually started. The product is now Boomerang's core offering, live today at getboomerang.ai.

Reflection
Strategy is deciding what not to build. Questioning the roadmap before designing for it felt uncomfortable at first - it wasn't my job on paper. It became the highest-leverage thing I did there.
Founder's Voice
I'm incredibly proud to know Vignesh as a phenomenal colleague and an incredible friend. Vignesh was one of the first people to join us at BuyerAssist (Boomerang) and someone who truly brought his full self into our small startup team. I'm a big fan of the passion and user-first perspective Vignesh brings to the whole decision-making process. He's a self-starter and someone who's always challenging himself and pushing the limits.- Shyam HN, CEO & Founder, Boomerang.ai
Next story
Turning a fixed dashboard into a rules engine sales teams could configure - Zoho

Happy to walk through the Persona 360 framework in more depth - it's the part I'd talk about longest.

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