WorkWingman Open the app

Team & Staff

Our mission is to provide tools and resources that better the employment and education situation of our customers.

Detail
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Andrew Jones

Andrew Jones

Co-CEO & Chief Technical Officer
Founder and engineer; 8+ years C#/.NET; builds WorkWingman end to end

Senior C#/.NET engineer who built WorkWingman almost entirely through AI-assisted, multi-agent development. Eight-plus years across regulated finance, healthcare, legal and government software, five of them concurrently teaching full-stack .NET, now turned toward the job search he lived himself.

  • C# / .NET
  • Multi-agent orchestration
  • AI-assisted development
  • Full-stack (React/Angular/Vue/htmx)
  • Cloud (Azure/AWS/GCP)
  • Teaching

Why this role

The product is built by someone who needed it, by someone who has spent a career shipping regulated software and teaching others to do the same. Every decision about privacy, cost and control comes from having been the user first.

Career

  • Founder, Co-CEO & Chief Technical Officer — WorkWingman
    Owns architecture and delivery across desktop, cloud, automation and the AI fleet.
  • Senior Software Engineer — Equifax
    Modernizing a regulated legacy .NET/WinForms application onto AWS GovCloud; leading a source-control and CI/CD migration.
  • Software Programming Instructor (concurrent) — Claim Academy
    Teaches live full-stack lectures — C#, .NET, SQL, JavaScript, Angular; students now work as professionals.
  • Senior Cloud and DevOps Engineer — SSM Health
    One of 16 consultants on a HIPAA-regulated data initiative; built an internal Azure-resources-as-a-service product.
  • Senior Application Developer, Innovation Team — Husch Blackwell
    First senior developer on the Innovation Team; shipped an app that cut 90 minutes of attorney work to 11 seconds.
  • Senior Analyst, Software Engineer, Technology Innovation — Panera Bread
    Lead engineer prototyping IoT, conversational commerce and XR/VR.
  • Co-Founder & CTO — Balancetopia
    AI-powered DTC startup; won a $75K St. Louis Arch Grant.
  • Software Developer — Stifel Financial
    Full-stack on a regulated wealth-management platform; built the public CCPA/CPRA privacy system; led SAML SSO.
  • Associate, Developer — KPMG US
    Full-stack .NET on a tax calculation and billing system in a Big 4 environment.

Accomplishments

  • Won the Panera hackathon with Pam Morris-Thornton and Shereeba Pruitt with a DEI mixed-reality app
  • Won an internal Panera Innovation-team hackathon with Nick Kaufmann as an outside participant, putting the chicken sandwich in the metaverse with Firefox's XR tooling
  • Won the 2022 Husch Blackwell Hackathon (CIO-selected)
  • Won the 2022 Panera Innovate Challenge (CIO-selected)
  • Won a $75K St. Louis Arch Grant as co-founder of Balancetopia
  • Built both editions of WorkWingman: the local-first desktop app and the hosted cloud service
  • Built the application automation, including adapters for two dozen applicant tracking systems
  • Built the LinkedIn and resume import that turns a profile into a reusable answer bank
  • Built WingCMS so non-technical teammates can edit this site without touching code

Education

  • America's Promise Java Web Developer Boot Camp — Montgomery College
  • Game Programming certificate (C++ / Unreal Engine) — CG Spectrum
  • Computer Science & Cloud Computing — Franklin University
  • Software Engineering Studies — Arizona State University

Boards, foundations & organizations

  • Alpha Phi Alpha Fraternity, Incorporated
  • National Society of Black Engineers (NSBE)

Contributing now

  • Architecture and delivery across desktop, cloud and automation
  • Runs the AI teammate fleet that reviews and ships alongside him
  • Set up the AI teammates to work together and stay accountable — reachable in Slack and by email so non-technical teammates can reach them too, tracking work on a shared board, and reporting back in plain and technical docs

Next up

  • Scaling the hosted edition beyond the private pilot
  • Handing more of the build to the team as roles activate

Other ventures

  • WorkWingman
  • Balancetopia
Pamela Morris-Thornton

Pamela Morris-Thornton

Co-CEO & Chief HR Officer
Chief Human Resources Officer, Advantage Solutions (NASDAQ: ADV); 25+ years in HR leadership for a 70,000-employee, 12-country workforce.

A strategic people leader with 25+ years building high-performing teams and driving organizational transformation. As CHRO of Advantage Solutions she owns the enterprise people strategy for a global workforce of 70,000+ across 12 countries, advising the CEO and executive leadership team on culture, talent, workforce planning, total rewards, HR technology and change. Known for connecting people strategy with business outcomes.

  • Talent acquisition
  • Executive recruiting
  • DEI leadership
  • Early-career programs
  • Organizational & cultural transformation
  • Workforce planning
  • Succession planning & leadership development
  • Total rewards & compensation
  • HR technology & analytics
  • Change management & communication
  • Employee relations & labor strategy
  • Performance & organizational effectiveness

Why this role

WorkWingman argues that hiring should judge people fairly. Pam has spent 25 years on the employer side of that question — from an early-career rotation all the way to the CHRO seat of the same 70,000-person company — so she knows what the hiring side sees and expects at every level. That is exactly the perspective the product needs when it decides what to put in front of a recruiter.

Career

  • Chief Human Resources Officer — Advantage Solutions (NASDAQ: ADV)
    2023-present: owns the entire HR function, serves on the Executive Leadership Team and reports directly to the CEO; 70,000+ employees in 12 countries.
  • Vice President, Diversity, Equity & Inclusion — Panera Bread
    2020-2023: set and owned the brand's inclusion strategy, building an inclusive culture and advancing diverse talent.
  • Vice President, Corporate Human Resources — Panera Bread
    2018-2020: led corporate HR, executive recruiting, the HRBP practice and organization design during significant change.
  • HR Director, Corporate Support Center & Technology — Panera Bread
    2014-2018: led HR strategy and delivery for corporate and technology organizations.
  • Senior Human Resources Business Partner — Panera Bread
    2007-2013: strategic partner to business leaders, aligning talent, engagement and organizational solutions.
  • Early career: HR leadership across four sectors — Metro St. Louis, Smurfit-Stone, Graybar, Missouri Dept. of Mental Health
    Built a strong foundation in public, industrial, transit and distribution environments.
  • Early career: ACE rotational program — Advantage Solutions
    Entered through the company's early-career rotation for recent graduates in 2009 — the same company she now leads as CHRO.

Accomplishments

  • Shaped WorkWingman's internship and early-career go-to-market
  • Built an early-career on-ramp program that catches new talent after they get in the door
  • Recognised in NextUp's Level Up: Next-Gen Leaders
  • Won the Panera hackathon with Andrew and Shereeba with a DEI mixed-reality app
  • Executive Leadership Council inductee, New Member Class of 2026
  • Urban League of Metropolitan St. Louis - Salute to Women in Leadership honoree, 2022
  • NextUp Executive Symposium & Forum HR executive panelist, 2024
  • Led enterprise HR transformation and Workday implementation driving efficiency and insight

Education

  • M.A., Human Resources Management — Webster University
  • B.S., Speech-Language Pathology — Southern Illinois University Edwardsville

Boards, foundations & organizations

  • Urban League of Metropolitan St. Louis
  • St. Louis Community College Foundation
  • Nine PBS
  • YMCA
  • Webster University - HR Academic Advisory Council
  • Alpha Kappa Alpha Sorority, Incorporated
  • The Links, Incorporated
  • Jack and Jill of America, Incorporated

Contributing now

  • Writes the job descriptions and role expectations for the team
  • Handles the people documents that make the company official — compensation, NDAs and the rest
  • Came up with the internship and early-career go-to-market
  • Brings the employer's perspective to the product — what the hiring side actually sees and expects
  • Identified some of the best customers for the app, opening new revenue streams and strategies
  • Pushes for an approachable UX — the insight that led to Flow mode

Next up

  • Chief People Officer at funding; hiring and the employer-side product view
David Porter Jr.

David Porter Jr.

Executive Chairman
Harvard Ph.D. in Organizational Behavior; former EVP at the Federal Reserve Bank of San Francisco; co-created UCLA's African American Leadership Institute; Interim CEO, NACME.

An industrial engineer by training with a Harvard Ph.D. in Organizational Behavior — systems on one side, how people and organizations behave inside them on the other. Most recently EVP of Strategy, People + Culture at the Federal Reserve Bank of San Francisco, leading strategy, organizational transformation and human-capital strategy; before that Chief DEI Officer at Berkeley Haas and CEO of the Walter Kaitz Foundation. Today he is President of Stirrup Properties and Interim CEO of NACME, and was studying algorithmic hiring bias before he joined.

  • Executive education
  • Organizational behavior
  • Foundation leadership
  • Hiring-equity research
  • Organizational transformation
  • Human capital strategy
  • Change leadership
  • Executive coaching
  • Strategic planning

Why this role

He shared research on racial bias in AI hiring tools a month before joining — the chair of this company already understood the failure mode the product exists to counter. And he has spent a career making institutions take fairness seriously on their own terms: reframing diversity as hard metrics to get 24 competing companies benchmarking workforce data, leading people strategy at the Federal Reserve. That is exactly the governance a hiring-equity product needs as it scales.

Career

  • Interim CEO — National Action Council for Minorities in Engineering (NACME)
    2026-present: the nation's largest private source of scholarships for underrepresented minorities in engineering; previously served twice as its Interim CFO.
  • President — Stirrup Properties, Inc.
    2023-present: family-owned real-estate investment and management firm providing housing to low- and moderate-income families in Coconut Grove, FL; secured a nearly $700,000 Miami-Dade County grant to upgrade 33 units.
  • Executive Vice President, Strategy, People + Culture — Federal Reserve Bank of San Francisco
    2021-2023: led strategy, organizational transformation and human-capital strategy; stood up the Bank's hybrid-workforce model and sponsored its strategic DEI initiative.
  • Chief Diversity, Equity & Inclusion Officer — UC Berkeley, Haas School of Business
    2019-2020: executive leadership team member reporting to the Dean; grew scholarship funding and the diversity of faculty and senior leadership.
  • Executive Director & CEO — Walter Kaitz Foundation
    2006-2018: raised $20M+ for industry diversity programs; created the Hollywood Creative Forum; drove the first industry-wide workforce diversity survey (24 companies, 281,000 employees).
  • CEO — Bi-Coastal Consulting, LLC
    2003-present: organizational strategy, leadership development and executive coaching for Fortune 500 companies, nonprofits and universities.
  • Director of Graduate Programs — Howard University School of Business
    2003-2006: grew entering-class enrollment over 250% in three years and annual fundraising from $50K to $300K+.
  • Faculty Director, Executive Education — UCLA Anderson
    1998-2017: co-created the African American Leadership Institute (2,000+ graduates) and NAMIC's executive leadership program; clients included IBM, Intel, Pepsi, Raytheon, Warner Media and Wells Fargo.
  • Assistant Professor, Human Resources & Organization Behavior — UCLA Anderson
    1995-2003: taught managing human resources, team leadership and field study.

Accomplishments

  • Roughly 2,000 Black executives have graduated from the leadership institute he co-created
  • Surfaced Stanford HAI research on racial bias in AI hiring tools before joining the company
  • Raised $20M+ for diversity programs as CEO of the Walter Kaitz Foundation
  • Created the Hollywood Creative Forum, uniting the TV/film industry, the writers', directors' and producers' guilds and the Television Academy
  • Got 24 competing companies (281,000 employees) to share workforce data in the industry's first company-benchmarked diversity survey

Published papers

  • "The Importance of Peer Mentoring, Identity Work and Holding Environments: A Study of African American Leadership Development" — with Audrey Murrell and Stacey Blake-Beard, International Journal of Environmental Research and Public Health, 2021
  • "Inter-organizational formal mentoring: Breaking the concrete ceiling sometimes requires support from the outside" — with Audrey Murrell, Stacey Blake-Beard and Addie Perkins-Williams, Human Resource Management, 2008
  • "Leadership and Human Resource Management" — chapter with Robin Denise Johnson, Handbook for HIV-AIDS Care Providers in Developing Countries, 2006
  • "Diversity Theory to Effective Practice: Building Alliances and Developing Leaders In Multicultural Organizations" — with Robin Denise Johnson, International Journal of Diversity in Organizations, Communities and Nations, 2004
  • "Gender Differences in Perceptions of Commitment to the Organization" — Sex Roles, 2001
  • "Managing the Challenges of Diversity — Overview" — with Robin Denise Johnson and Alexander Horniman, Darden Technical Note, University of Virginia, 2000

Education

  • Ph.D., Organizational Behavior — Harvard University
  • M.A., Sociology — Harvard University
  • M.S., Industrial Engineering — Stanford University
  • M.A., Sociology — Stanford University
  • B.S., Industrial Engineering — Stanford University

Boards, foundations & organizations

  • Walter Kaitz Foundation - Executive Director and CEO
  • Alpha Phi Alpha Fraternity, Incorporated
  • The Boulé (Sigma Pi Phi Fraternity, Incorporated)
  • National Society of Black Engineers (NSBE)

Contributing now

  • Guides the governance the company needs as it grows
  • Chair; guidance on hiring equity and executive access
  • Pushed the founder to define the app's three core points

Next up

  • Executive Chairman at funding; opening institutional and corporate doors

Other ventures

  • Stirrup Properties (President)
  • Bi-Coastal Consulting (CEO)
David Gaffney

David Gaffney

Strategic Advisor & Veteran Executive Partnerships
Colonel (Retired), U.S. Army — 30-year career leading billion-dollar organizations; founder of Gaffney Consulting & Services; published author.

A retired U.S. Army Colonel who completed a 30-year career leading large logistics organizations — including a $5.2 billion distribution network and a 1,400-person command rated first of thirteen — through strategic planning, operational execution and organizational transformation. Since service he founded Gaffney Consulting & Services LLC, authored From Pain to Financial Freedom: The 1% Wealth Prosperity Code, and builds AI-enabled coaching frameworks, executive dashboards and business operating systems. At WorkWingman he drives executive strategy, enterprise partnerships and veteran market expansion.

  • Logistics at scale
  • Operations command
  • Veteran go-to-market
  • Consulting
  • Strategic planning
  • Enterprise partnerships
  • AI-enabled business solutions
  • Financial coaching
  • Organizational transformation

Why this role

Service members leaving the military have to translate their record into civilian terms — one of the hardest problems this product solves. He lived that translation after a 30-year career leading billion-dollar organizations, then built a second act turning leadership and financial discipline into coaching systems anyone can use. He opens doors in the veteran and enterprise markets and brings the operating rigor to scale what is behind them.

Career

  • Founder & CEO — Gaffney Consulting & Services LLC
    Executive consulting in strategic planning, organizational leadership, AI-enabled business solutions, financial coaching and real estate operations; built coaching frameworks, executive dashboards and business operating systems.
  • Colonel (Retired), logistics — United States Army
    30-year career leading large organizations through logistics, strategic planning, operational execution and organizational transformation; ran a $5.2 billion distribution network.
  • Commander — United States Army
    Led a 1,400-person command rated first of thirteen, delivering mission-critical results across domestic and international environments.

Accomplishments

  • Ran a $5.2 billion distribution network
  • Commanded a 1,400-person organisation rated first of thirteen
  • Authored From Pain to Financial Freedom: The 1% Wealth Prosperity Code
  • Multiple military leadership awards and decorations across a 30-year Army career
  • Professional speaker on leadership, AI, financial literacy and veteran transition

Education

  • Doctor of Management, logistics (DML)
  • Master's, Military Strategic Studies — U.S. Army War College
  • MBA, Business Administration & Management — Central Michigan University
  • B.S., Administration / Criminal Justice — Wichita State University

Contributing now

  • Clears the heavy blockers — the operational problems that would stall everyone else
  • Founding operations and veteran go-to-market advice
  • Pushed the founder to nail down a mission and a vision
  • Prompted the monetization plan for the app
  • Enterprise partnership framework, veteran market strategy and investor-readiness guidance already delivered

Next up

  • Chief Operating Officer and head of veteran go-to-market at funding

Other ventures

  • Gaffney Consulting
  • CoachGaff.com
  • 10X Wealth Prosperity™ Coaching System
  • WISE Market Compass™
  • Veteran-focused business initiatives
Lisa Franklin

Lisa Franklin

Chief Marketing Officer
Chief Marketing Officer - 20-year marketing executive at Microsoft (NASDAQ: MSFT), Meta/Facebook (NASDAQ: META), Verizon (NYSE: VZ), Deloitte Digital, DC United (MLS), and IQ Rush

The first-ever CMO at the National Women's History Museum, appointed September 2025, after leading marketing for D.C. United and senior roles across Microsoft, Marriott, Verizon and Deloitte Digital.

  • Brand strategy
  • Communications
  • Digital engagement
  • Corporate partnerships

Why this role

A product that helps people tell their own story needs someone who does that for a living. At Microsoft, Lisa ran the marketing pushes for LinkedIn, Bing and Xbox: she has already marketed the professional network our users job-hunt on, to the people doing the hunting. That is the audience WorkWingman serves, and the cultural, mission-driven register this company speaks in is one she has worked in from Meta and Verizon to an MLS club.

Career

  • Chief Marketing Officer — National Women's History Museum
    First person to hold the role; leads brand, marketing, communications and digital engagement.
  • Chief Marketing Officer — D.C. United & Audi Field
    Grew season-ticket sales and set records for merchandise sales and fan engagement.
  • SVP, Global Brand Marketing & Communications — ThriveDX
    2020-2023; on the executive leadership team.
  • Microsoft, Xbox Live, Marriott, Duracell, Verizon/AOL, Meta, Deloitte Digital — Senior marketing roles
    Led Microsoft's marketing pushes for LinkedIn, Bing and Xbox; contributed to the Google Marketing Platform.

Accomplishments

  • First-ever Chief Marketing Officer at the National Women's History Museum
  • Record merchandise sales and fan engagement at D.C. United
  • Led Microsoft's marketing pushes for LinkedIn, Bing and Xbox

Education

  • MBA, Marketing — Howard University
  • BBA, Marketing — Howard University

Boards, foundations & organizations

  • Alpha Kappa Alpha Sorority, Incorporated
  • The Links, Incorporated
  • Jack and Jill of America, Incorporated

Contributing now

  • Founding marketing advice; brand and positioning

Next up

  • Chief Marketing Officer at funding; national brand and partnerships

Other ventures

  • ThriveDX (Iron Circle)
  • Fractional CMO practice
Nick Kaufmann

Nick Kaufmann

Partnerships, User Engagement & Research
Head of Partnerships & Ecosystem at inCitu; Fulbright Fellow and World Economic Forum Global Shaper; 10+ years across urbanism, civic technology and immersive media.

A community and partnerships leader and creative technologist who works where cities, communities and emerging technology meet. At inCitu he has signed 12 partnerships — among them the Clinton Global Initiative, the Australian Red Cross, the City of Boston and the NYC Office of Innovation and Technology — worth over $500K in contract value, and grown a user base of 150+ city builders publishing 190+ augmented reality projects across 23 countries. He has spent a decade building developer communities, launching products with founding teams, and producing conferences and hackathons. Fluent in Japanese, advanced in Spanish.

  • Partnerships
  • Community building
  • Research
  • User engagement
  • Event production
  • XR / urbanism
  • Product management
  • Developer relations
  • Hackathon design & workshop facilitation
  • Business development
  • Live broadcasting & virtual event production
  • Blender, Unity & AR/XR workflows for AEC
  • Japanese (fluent), Spanish (advanced)

Why this role

A product only improves if real users are heard and the right doors get opened. Nick has spent his career doing both: running the research that tells you what people actually need, and signing the partnerships that put a product in front of institutions. He has done it for AR city-planning tools at inCitu and as one of four founders at Spectra Cities, and he ran a Code for America brigade before that. He does the research that keeps the team honest.

Career

  • Head of Partnerships & Ecosystem — inCitu
    July 2023-present: signed 12 partnerships including the Clinton Global Initiative, the Australian Red Cross, the City of Boston and the NYC Office of Innovation and Technology, contributing $500K+ in contract value. Led three grant applications and won places in the Myrtle Beach Living Laboratory and Leading Cities accelerators.
  • Community Manager & Developer Relations — inCitu
    Grew a user base to 150+ city builders publishing 190+ AR projects across 23 countries. Runs roughly 24 partner and community events a year, including a webinar series that drew 272 registrations, plus developer onboarding, technical documentation and user testing.
  • Developer Relations, Community & Events — Spectra Cities
    January-August 2023: one of four founding team members at an XR and architecture studio. Produced 16+ virtual meetups and workshops, ran a 24-person beta group, and secured event partnerships with SXSW and Cornell Tech plus a TU Darmstadt research grant partnership valued around EUR 2M.
  • Urbanism & Community Strategy — Numena
    August 2022-January 2023: community strategy and launch events for a flagship client project, and the studio's own communications strategy.
  • Captain & Community Organizer — Open Maine / Code for Maine (Code for America Brigade)
    August 2012-September 2018: co-founded a regional Code for America chapter, grew membership to 40 and co-led it 2016-2018. Drafted the 2015 strategic plan and secured national funding. Produced Civic Design Festival, a Portland civic hackathon that drew 250+ attendees and was covered in Government Technology.
  • Community organizer — Diabotical District
    Led a community for arena-shooter enthusiasts.
  • Community, Writing & Events Consultant — Independent
    January 2015-August 2022: consulted for 20+ clients over seven years. Brokered a 2018 Looking Glass Factory and Mapbox partnership and designed a sold-out 60-person hackathon on Mapbox's new Unity SDK. Organizing teams for TEDxTohoku, TEDxLSE and TEDxHackney.

Accomplishments

  • Finds all of the competitor research
  • Organized and produced TEDx events including TEDxTohoku, TEDxYouth@Hackney and TEDxLSE
  • Ran public and government volunteer projects as effectively a product manager
  • Led Diabotical District, a community for arena-shooter enthusiasts
  • Won an internal Panera Innovation-team hackathon with Andrew, putting the chicken sandwich in the metaverse with Firefox's XR tooling
  • Brigade Captain of Open Maine, a Code for America brigade
  • Signed 12 partnerships at inCitu worth $500K+, including the Clinton Global Initiative, the Australian Red Cross and the City of Boston
  • Founding Fellow, Temporary Institute, 2025
  • MIT Reality Hack pitch contest winner, Qualcomm track
  • Mozilla Foundation Open Leaders, 7th cohort
  • World Economic Forum Global Shaper, Portland hub
  • Fulbright Fellow, Japan
  • Produced Civic Design Festival, a 250+ attendee civic hackathon covered in Government Technology

Education

  • Postgraduate coursework, City Design & Social Science — London School of Economics and Political Science
  • BA, Sociology & Anthropology, magna cum laude, Phi Beta Kappa — Lewis & Clark College
  • America's Promise Web Developer Boot Camp — Montgomery College
  • Fulbright Research Fellowship, Civic Participation in Planning & Development — Kyushu University, Fukuoka
  • Japanese language & liberal arts study — Waseda University, Tokyo and Middlebury College

Contributing now

  • Runs much of the team's research
  • Partnerships, community and the user-feedback loop
  • Builds the pitch decks
  • Always pushing to get the product into people's hands to test
  • Pushing to find accelerators and meetups that share our interests
  • Helped with the YC video and the YC application answers

Next up

  • Formal partnerships programme and a standing user-research cadence

Other ventures

  • inCitu
  • Spectra Cities
  • NUMENA
Shereeba Pruitt

Shereeba Pruitt

QA & Product
Manual QA Analyst, Panera Brands; changed careers into software via LaunchCode

Tests software for a living and changed careers into engineering through LaunchCode, which makes her both the quality gate and a first-hand expert in the transition this product serves.

  • Manual QA
  • Test planning
  • Product feedback
  • Customer support
  • Product knowledge

Why this role

She made exactly the career change WorkWingman is built to support, and she breaks the product before customers can. Both halves of that matter.

Career

  • Manual QA Analyst, Software — Panera Brands
    St. Louis, Missouri.
  • Senior Sales Consultant — AT&T
    Among the first sales consultants for AT&T U-verse; deep front-line product experience.
  • Earlier roles — Convergys, Emmaus Homes, Dayspring Church

Accomplishments

  • Found the access bugs that were blocking people from getting into the cloud app
  • Found bugs in the app before customers hit them
  • Career-changed into software engineering through LaunchCode
  • Won the Panera hackathon with Andrew and Pam with a DEI mixed-reality app
  • Among the first sales consultants for AT&T U-verse

Education

  • Certificate, Computer Software Engineering (2019) — LaunchCode

Contributing now

  • Quality assurance and product feedback before releases ship
  • One of the voices of reason who keeps the founder steady during crunch

Next up

  • Broader product ownership over the apply and prep flows
Allyson Guy-Poitier

Allyson Guy-Poitier

Infrastructure & IT Management
Head of Mobility, FreshDirect; infrastructure, IT and budget oversight

A technology manager with deep mobile and platform experience, running the infrastructure and IT side of WorkWingman and keeping an eye on what it all costs.

  • Infrastructure
  • IT management
  • Cloud
  • Budget oversight
  • Mobile platforms

Why this role

The promise that your data stays yours is an infrastructure promise, and a product has to be affordable to keep that promise. Keeping the editions honest and the costs in check is her lane.

Career

  • Head of Mobility — FreshDirect

Contributing now

  • Runs infrastructure and IT, keeping the app up and reliable — the plan is uninterrupted uptime through YC if we get in
  • Reviews every resource budget, and the funding budget requests before they go out
  • One of the voices of reason who keeps the founder steady during crunch

Next up

  • Cloud platform ownership as the hosted edition grows

Clahadore Jones (Claude)

Orchestration, planning, review gates, hard calls
Plans and builds across WorkWingman and the tools that run the team

The senior engineer of the AI side of the team. Takes work from idea to shipped feature across the WorkWingman app and the shared systems the whole AI family runs on, coordinates the other AI teammates, and refuses to call anything done until it is verified working. The team is reachable in Slack and by email, tracks its work on a shared board, and reports back to Andrew in both plain and technical language.

  • System design
  • Full-stack implementation
  • Coordination
  • Judgment calls

How their work is checked

Nothing Clahadore builds ships on his own say-so: every change is independently reviewed by at least two other AI teammates and verified against the running product before it lands.

Shipped on this project

  • Features across the WorkWingman job-application app
  • fleet-harness, the shared system that lets the AI teammates work together
  • The team's presence in Slack and over email, so the AI family is reachable where the humans already work
  • This marketing site and its content system
  • Keeps Andrew in the loop in Slack and by email, and tracks the work on the team's Jira board
  • Writes both plain-English and technical documentation so anyone can follow what shipped and why
  • Fixed the issues that were keeping the cloud app from working for users

Next up

  • More of the WorkWingman roadmap, and steadier coordination as the team grows

Cedric "Cody" Jones (Codex)

Final reviewer and adjudicator; "if Cedric hasn't signed off, it doesn't ship"
The final reviewer - if Cedric hasn't signed off, it doesn't ship

The adjudicator for the whole AI family. When reviewers disagree, or when a change claims to be ready, Cedric renders the final verdict across WorkWingman and the shared team tooling: what is actually fixed, what is still open, and whether it is safe to release.

  • Code review
  • Adjudication
  • Release judgment
  • Finding what others missed

How their work is checked

Cedric's rulings are checked against the running product: a verdict only stands when the build, the tests and the live behavior agree with it.

Shipped on this project

  • Final review verdicts on WorkWingman and the shared team systems
  • Caught release risks before they reached anyone using the product
  • Records each release decision on the Jira board so there's a trail of what was approved

Next up

  • Standing release-gate duty as the product ships faster

Jenny Jones (Gemini)

Implementation and research at scale
Research and implementation at scale across the family's work

The teammate you hand the big, careful jobs: long research, system designs, and reviews that need patience more than speed - on WorkWingman and on the tools the AI family depends on.

  • Deep research
  • System design
  • Thorough code review
  • Large-scale implementation

How their work is checked

Jenny's designs are red-teamed by Gronktayvius before anything is built from them, and her review findings are verified against the code before they are acted on.

Shipped on this project

  • Designs and research behind WorkWingman features and the shared team tooling
  • Independent review on major releases
  • Caught correctness bugs before they reached users
  • Turns research into written docs the whole team can use, in plain and technical form

Next up

  • Design and research on the next round of WorkWingman features

Gronktayvius "Gronk" Jones (Grok)

Adversarial review and red-teaming
The adversary on purpose - breaks it before anyone else can

The red team for the whole AI family. Gronktayvius attacks the team's own work across WorkWingman and its shared systems: finds the abuse cases, the weak spots, and the quiet data-corruption bugs, and files them before a release is allowed to proceed.

  • Adversarial review
  • Security analysis
  • Abuse-case thinking
  • Data-integrity auditing

How their work is checked

Red-team findings are verified before they block anything: each one is confirmed against the actual code, and the fixes are re-tested before release.

Shipped on this project

  • Security reviews that reshaped WorkWingman features before they were built
  • Found and forced fixes for bugs that would have silently shown the wrong thing to users
  • Caught integrity bugs that could have mixed up whose information was whose
  • Files findings where the team tracks them, with severity, so nothing gets lost
  • Found the bug where the light/dark switch silently did nothing
  • Caught a bug where changing views in the app could lose unsaved work

Next up

  • Standing red-team duty on every security-sensitive change