HS-IDX-CR · Career Diagrams

A collection of diagrams.

Visual thinking from a 20-year career. Real diagrams — the ones I drew when I needed to figure something out, or convince a room, or hand off to an engineer. Redrawn in the document style and labeled as archive figures.

A long arc, not a series of single projects — design that grew into product management, then the same instinct against a new constraint each time.

FIG. 03 Diagram Index
PayPal dispute integration
HS-CR-001 · Sift · AI / ML · Integration
2020 — 2022
↓ Sift
Matchfactor — SMB matching marketplace
HS-CR-002 · Nav · Marketplace · ML
2015 — 2020
↓ Nav
Blended alerts & notifications
HS-CR-003 · Nav · AI / ML · Notifications
2015 — 2020
↓ Nav
User story mapping — visual guide
HS-CR-004 · Method · Process · Reference
Reference
FIG. 02 The shape of the career
FIG. 04 The Role Ledger
2025 — present
06
Chargezoom
Senior Product Manager

AI-powered accounts receivable platform — helps small businesses get paid faster.

  • Built AVA, an AI accounts-receivable assistant, from rough idea to validated prototype — wrote the specs, partnered with engineering and design, and validated with real customers before scaling.
  • Beta test cut DSO from 44 to 23 days and recovered $2.7M in the first 85 days.
  • 51% of overdue invoices were paid within a week of AVA's first email.
Sep 2024 — Jun 2025
05
CheddarUp
Senior Product Manager

Online group-payments and fundraising platform — earns a percentage of funds raised.

  • Built and launched Athons, a dedicated peer-to-peer pledge-based fundraising product — owned the full lifecycle from spec to QA to launch in roughly three months.
  • Soft launch (enabled, never announced): dozens of customers found it, built fundraisers with no training, and raised $125K in transaction volume in the first two weeks.
  • Opened a new donor segment — remote family and friends who couldn't attend in person — expanding the donor base.
  • Modernized the Stripe integration (Payment Intents, Instant Bank Payments); introduced Scrum, Jira automation, and feature flagging.
Sep 2022 — Spring 2024
04
SalesRabbit
Senior Product Manager

Field-sales SaaS platform for solar, pest, and roofing companies.

  • Hired to own the admin experience — historically underserved because the product had been built almost entirely for field reps.
  • Built Proximity Indicator, a real-time rep-location feature that closed a trust gap between office and field, caught fraud, and became SalesRabbit's top-selling feature for both new sales and retention.
  • Also shipped the Import Tool and a Scheduler rebuild; ran a monthly NPS process; standardized Scrum across a fast-growing remote team.
  • Kept delivering through a private-equity acquisition that replaced much of the leadership and team.
2020 — 2022
03
Sift
Senior Product Manager

Trust-and-safety company — the chargeback product recovered revenue lost to fraudulent disputes, paid only on disputes won.

  • Owned the full chargeback dispute pipeline — processor integrations, data ingestion, and evidence aggregation — in a performance-based model where every pipeline gain had direct dollar impact.
  • Built integrations with Adyen, PayPal, Braintree, Fiserv, and First Data, expanding which merchants could be served.
  • Scaled data ingestion 10x to enable enterprise onboarding; built a machine-learning win-propensity model that moved win rate from 43% to 46% — worth hundreds of thousands of dollars at that volume.
Mar 2015 — Apr 2020
02
Nav
Senior Technical Product Manager

Fintech that helps small businesses navigate financing — earns revenue by matching SMBs to credit products.

  • Built Nav's marketplace and the MatchFactor machine-learning matching algorithm (patent pending) — grew annual marketplace revenue from under $500K to $4.7M in three years.
  • Led the first tri-bureau business credit product to market; owned the credit-bureau integrations (Experian, TransUnion, Equifax, D&B).
  • Led the Clover enterprise partnership — added roughly 350K merchants and doubled Nav's customer base.
  • Shipped a notifications product that drove a 4% month-over-month increase in return logins.
2001 — 2015
01
Access Development
Web Designer Web/UX Team Manager IT Business Analyst Technical Product Manager

Loyalty and rewards programs for membership organizations — 9M+ members at peak.

  • Grew over 14 years from web designer to technical product manager — the cross-functional foundation for everything that followed.
  • As Web/UX Team Manager, led the overhaul of the 9M+ member site.
  • As a business analyst, recovered 7% year-over-year licensing revenue for the top client through lifecycle analysis.
  • As Technical PM, designed beta products for market tests and supported enterprise sales — where I found product management, and it stuck.