The problem

Webgility is B2B fintech SaaS that syncs sales, inventory, and accounting data for ecommerce sellers across marketplaces like Amazon, Shopify, and Walmart, and accounting platforms like QuickBooks and Xero. The product delivered real value, but customers struggled to experience it. Onboarding required understanding technical concepts like API configs and sync rules before ever seeing payoff. UI and messaging were inconsistent across the app, account portal, and website. Pricing didn't reflect the value the product actually delivered to larger accounts.

My approach

I owned positioning, messaging, pricing and packaging, lifecycle marketing, and sales enablement, working in close partnership with the UX and design team redesigning onboarding and settings around a clearer aha moment, and with customer success on voice-of-customer and panel-based message validation.

I also led a company-wide Packaging, Pricing, and Positioning initiative to fix a structural problem behind the confusion: a sprawling, feature-based plan lineup, split across separate desktop and online pricing ladders with per-user upcharges, that made it hard for customers to know what they needed. I rebuilt the positioning around we sell solutions, not products, mapped detailed buyer personas to each tier, and benchmarked pricing against direct competitors. That case was grounded in real usage data: customers using Webgility's real-time automation saved up to 10 hours a week on manual processes on average and grew order volumes 651% in their first year, evidence that made the upmarket case easy to defend internally and with customers.

Miro board mapping customer needs to QuickBooks version to Webgility plan tier
The tier-mapping logic behind the repackaging: what a customer needs to do, mapped to their QuickBooks version, mapped to the right plan.

What I did

  • Repositioned the product upmarket through new pricing, packaging, and value communication, without sacrificing new subscription volume
  • Rebuilt onboarding messaging and lifecycle touchpoints around the redesigned value-moment experience, shortening the path from signup to conviction
  • Led a company-wide Packaging, Pricing, and Positioning initiative, collapsing a sprawling, feature-based plan lineup across both product lines into simplified, customer-centric tiers
  • Built detailed buyer personas for every customer segment, from solo sellers to multi-channel, multi-warehouse operations, mapping pain points, objections, and willingness to pay to each tier
  • Built and maintained a competitive battlecard program covering seven-plus direct competitors, equipping sales with feature, pricing, and positioning comparisons
  • Built a partner marketing program with Intuit, Shopify, Amazon, and Walmart
  • Led customer marketing programs to drive deeper feature adoption
  • Championed HubSpot company-wide, driving cross-functional adoption across marketing, sales, and support

See the format behind that battlecard program. I rebuilt this competitive intelligence work as a sample called the Ledgerly battlecard. It's illustrative: the real competitor names, pricing, and win/loss data behind the original program are proprietary to Webgility, so this version uses a fictional product and competitor to show the thinking and format without exposing confidential business information.

View the sample battlecard
Webgility positioning and messaging framework document
The positioning and messaging framework used to align product, sales, and marketing on the new story.

Results

110%Increase in average selling price, from repositioning and repackaging the entire product lineup upmarket, without reducing new subscription volume
150%Increase in sales win rate from new competitive battlecards, enablement, and training
45%Year-over-year pipeline growth from full-funnel strategy and sales alignment
$2MNew pipeline from the Intuit, Shopify, Amazon, and Walmart partner program
31%Increase in high-converting leads from app store and organic growth
26%Increase in trial-to-paid conversion through customer journey optimization and lifecycle improvements
18%Increase in core feature adoption from customer marketing programs
10 monthsPromoted from Director of Product Marketing to Head of Marketing

Repositioning a technical product upmarket only works if pricing, messaging, and the actual customer experience move together. The redesigned onboarding experience gave customers a faster path to value. Positioning and packaging gave them a reason to pay more for it. Neither alone would have moved average selling price 110%.