Chief Technology Officer

IndeVets | Philadelphia, PA | September 2023 - Present

I lead Technology at this PE-backed, 3x Inc. 5000 HealthTech company, architecting a capital efficient strategy to maximize enterprise value. To execute this, I built the entire Product & Technology organization, transitioning from an external agency to a high performing in-house unit, and led the full scale migration to a modern GCP tech stack.

• Conceived of and built the proprietary algorithmic optimization engine, backed by machine learning, that enabled a strategic pivot in the company's business model, creating a data driven playbook for scalable, de-risked market expansion.
• This model drove top line growth by enabling accurate geo-targeting of new hospital customers and bottom line efficiency by precisely modeling veterinarian supply and demand, leading to a substantial reduction in SG&A expenses and precise targeting of recruiting and marketing efforts.
• Led the development of the company's foundational technology stack and ecosystem, including a new core staffing platform, veterinarian mobile app, and a comprehensive data warehouse with full back office integration (Salesforce, Hubspot, PayCor, iCIMS).

Managing Partner - Fractional CTO

Accelerator CTO | Philadelphia, PA | June 2021 - September 2023

Founded a successful advisory practice providing technical and product leadership to high growth companies. My approach centered on three pillars: establishing clear product roadmaps, implementing pragmatic agile methodologies, and mentoring founders and technical leaders to build self sustaining organizations and de-risk the path to scale.

• Guided Beneration in building its first in-house engineering team, successfully insourcing all development.
• Modernized the engineering processes and technology stack for vehicle routing platform Hailify to support its rapid growth.
• Directed the technology strategy for The Burnratty Investment Group's HealthTech AI ventures, including the development of an XRP blockchain solution.
• Led the technical due diligence for the private equity evaluation of IndeVets, that directly led to my recruitment into their leadership team.

Director of Engineering, Consumer Product

goPuff | Philadelphia, PA | January 2019 - June 2021

Joined at the Series C stage to lead all consumer facing Engineering and UX for the core mobile app, website and marketing tech. Was a key leader during a period of historic hypergrowth as the company raised $3B and its valuation skyrocketed to over $9B.

• Scaled the Product & Engineering organization from a shoestring team of 7 to over 200, building the world class organization required to meet explosive global demand.
• Championed and built the company's first product experimentation platform, enabling a data driven A/B testing approach that led to a multiple percentage point lift in Average Order Value (AOV).
• Led a full scale, cross functional brand rebuild with marketing and design, and rebuilt the company's loyalty program to significantly increase customer retention.

Chief Technology Officer

IncentFit | Philadelphia, PA | April 2015 - October 2018

Recruited as the first technology leader, I built and scaled the IncentFit platform from an MVP into a successful, high volume corporate wellness solution serving over 200 corporate clients, including Corning and Blue Cross Blue Shield.

• Architected and built the company's core financial engine: a complex micropayments system that securely processed over $500 million in funds annually.
• Developed a sales onboarding tool that enabled the instant creation of custom wellness plans, directly resulting in a significant increase in client conversions.
• Engineered a robust data ingestion platform with multiple data pipelines to unify health data from dozens of sources, including Fitbit, Garmin, Apple Health, and Google Fit.

Founder & CTO

BitsDuJour | New York, NY | 2007 - 2015

Pioneered one of the first "flash sale" e-commerce platforms, creating a new go-to-market channel for the Independent Software Vendor industry. Built the business from the ground up, leading all product, technology, and marketing operations.

• Engineered a high volume marketing automation platform that delivered 500,000+ emails daily.
• Grew and managed a cross functional team of six, leading the company to win the "Best Independent Software Vendor Service Award."
• After eight years of profitable, self sustaining operation, I led the company through a successful exit.

Founder & CTO

Iconico, Inc. | New York, NY | 2003 - 2008

As my first entrepreneurial venture, I founded Iconico to build and market a suite of award winning UX and development software tools, identifying a clear market need for specialized developer utilities.

• Led the entire product lifecycle for a portfolio of tools, including industry standards like Screen Calipers and ColorPic, which garnered hundreds of thousands of downloads.
• Grew the business into a profitable and fully automated operation with outsourced support, enabling a transition to passive ownership.

Early Career Highlights

Various Roles including VP of UI Design, Lead Design Technologist & UX Consultant | New York, NY | 1999 - 2010

During the dot-com boom and its aftermath, I held progressively technical leadership and consulting roles at prominent agencies and tech companies, leading high profile digital projects for world class brands.

• Built the UX for Forbes.com (Rare Medium).
• Directed the UI team for a complex insurance platform (Riskclick).
• Built the first WebMD Symptom Checker.
• Led platform migrations of WWD.com and Brides.com for Conde Nast (FIS).
• Architected a streaming media framework (MusicNet).
• Led major UX initiatives for brands including Cuervo, Philips, and the New York State Lotto (Tribal Worldwide).
• Developed the UI for FYE's in store touchscreen media station for SapientRazorfish.
• Additional consulting engagements with IAC, SchoolNet, Phizer, Connectify, Arcweb, Massify, Carbon CG, Hanft Raboy, and LawyerLink LLC.

Guest Lecturer, Emeritus CTO Program

Wharton Executive Education & Cambridge Judge Business School | October 2022 - Present

I develop and deliver sessions for senior technology leaders focusing on the critical strategic tradeoffs in high growth environments, covering key topics such as: balancing velocity against risk, managing technical debt as a financial instrument, and scaling engineering organizations from MVP to enterprise readiness.

Bachelor of Arts

Oxford Brookes University | Oxford, UK | 1996 - 1999

Degree show available at nicowesterdale.com/hyperlight