Interactive CV
Tim Naughton
Math/physics-native operator who has turned early-stage bets into industry standards — first non-founder at MyFinance, first non-founder business hire at Jane Technologies, and co-founder of Heady, a cannabis marketing agency running on the proprietary HeadyOS AI platform.
$10M → $600MJane's valuation across Tim's tenure — first non-founder business hire
#1Salesperson at Jane, by far
8-figure exitMyFinance acquired by Red Ventures, 16 months from Tim’s start
+128%Quarterly revenue growth on GLG's FBS team, to $1.8M+/quarter
Signature moves
The playbook, in four moves.
Reframed how Jane sold its e-commerce software
Demanded attribution analytics from product and rebuilt the presentation strategies the rest of the sales team went on to inherit.
Launched Jane's ad business
Jane Digital Merchandising — Jane's #1 single revenue generator at its peak, exceeding the original e-commerce subscription business.
Key decision-maker on GLG's Consultations platform
Worked alongside Engineering on requirements, workflow design, and rollout of the new self-serve, customer-facing product.
Ultra-low churn at Heady
3–5 clients lost across 4 years, surviving major leadership turnover at nearly every client brand.
Career, in order
Fifteen years, ten roles.
Co-Founder & CEO
- ~$108k/yr per retainer ($9k/mo) as the standard contract size.
- 3–5 clients lost across 4 years — ultra-low churn, surviving major leadership changes at nearly every client brand.
- $90k/mo → $1.1M/mo email-attributed revenue for a 6-store retail chain via Alpine IQ lifecycle work.
Fundraising / Advisor
- "I helped raise the capital that got them cash-flow-positive." Adds a CPG + fundraising dimension to Tim's operator profile that the Jane / Heady story doesn't cover.
- "I named it, I designed the mark, I hired the designer, and I co-designed the packaging." Anchor story for the Portfolio Design case study. The double-meaning brand name and the smiley-flower mark are Tim's; the polish is a hired designer's.
Head of New Business
- Jane Digital Merchandising was Jane's #1 single revenue generator at its peak — exceeding revenue from the original e-commerce subscription business. This is the headline number.
- Jane has since acquired other revenue streams (Jane Pay cashless-ATM per-transaction revenue is one example) after Tim's tenure; current ranking is unverified from outside the company.
- "I launched what became Jane's #1 revenue generator at its peak." Ask Tim for the full arc: MVP thinking, which clients he talked to, why the bid-to-top model beat the flat-rate placement model.
Head of Data Growth
- "Data monetization when it was still a niche discipline." The Infonomics certificate + Snowflake rollout are the mechanism.
- "Why standardized cannabis data matters." Tim published a 2020 LinkedIn article on this exact topic (see `profile/social-proof.md`).
General Manager
- #1 salesperson at Jane, by far, throughout the GM role — held the top spot until being pulled onto new product lines. (Prior drafts of the codex claimed a specific dispensary-count percentage; Tim's preferred framing is "#1 by far" because the exact percentage would need independent verification.)
- Sales in ~15 months — Tim held the sales-focused portion of the GM role for roughly 15 months before being pulled onto new product lines.
- Started including him on VIP / whale sales calls outside his territory because of demonstrated close rate.
VP of Sales and Business Development
- Grew publisher inventory from bloggers → mid-tier sites → CNN Money, MSN Money, Yahoo Finance.
- 8-figure acquisition, December 2017, by Red Ventures — subsequent to Red Ventures' Bankrate.com acquisition. 16 months from Tim's start date.
- Why Red Ventures bought: MyFinance was stealing placements from Bankrate — but generating so much more demand from those placements that even after rev-share, Red Ventures was making more money than before. Buying MyFinance brought the knowhow in-house.
Strategic Partnerships / Enterprise Sales
- On the sales leaderboard in 5 out of 6 quarters (Q1 2015 – Q2 2016) — the peer set was Civitas' Top 5 enterprise sales performers.
- Instrumental in landing Arizona State University, the largest contract in Civitas' history at the time and Civitas' first enterprise deal over $1M ARR.
- "Arizona State — the first million-dollar deal." Ask Tim for the full arc. This is a marquee story he underweighted in earlier CV versions and should feature prominently.
Research Manager & Team Lead, Financial & Business Services
- +128% quarterly revenue growth on the FBS team over 15 months.
- Grew FBS quarterly revenue to over $1.8M/quarter.
- Team composition: Research Managers and Research Associates, most fresh out of college.
Vice President / de facto CFO
- Grew the Staples EasyTech pilot from 2 stores in MD → 10 stores in FL → 200 stores in CA.
- Secured commercial financing to build 200 CyberSpa machines and deploy them into Staples stores — unlocking growth with limited cash on hand.
- Handshake deal in place for expansion to 1,400+ Staples stores — would have been "millionaires overnight."
Analyst
- Reconciliation process compressed from 3 hours to 30 minutes (starting at 5 AM). Confirmed with Tim.
- Still in production 16+ years later — Tim's process has outlived every colleague from that era at Brown Advisory.
- "Still in production 16 years later" — the origin of Tim's systems-first operating style. Ask him to walk through what the process actually did and how he cut it.
Awards & recognitions
The record, where it was official.
Long Distance Runner (Jane 2019) — longest deal cycle, most curveballs, most difficult RFP.
Jane TechnologiesWhale Hunter (Jane 2018) — consistently landing enormous brands with large ARR.
Jane TechnologiesEducation
Where the foundation was built.
University of Pennsylvania
BA, Philosophy, Politics & Economics — Globalization concentration
The Gilman School
Baltimore, MD — finished 3rd for Valedictorian
Quantic School of Business & Technology
Executive MBA