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Chris Winslett
@christopherwinslett
📍 Birmingham, AL

About

I’ve spent most of my career at the intersection of revenue, product, marketing, and sales at startups. I've spent some time with large companies spinning out new products and helping them become as effective as startups. The best results usually come from a focus on product usage and practical execution over years.

My favorite way to start a role is to dig into a research project to understand what revenue and usage flows are currently working. Then, focus on stripping away any barriers from that flow. Maximizing what currently works is always cheaper than bootstrapping new paths or rescuing failures. It sounds simple, but my unique ability to cut through data is my superpower.

Whether I’m on a small team building a technique product with a targeted launch date or leading a team of data engineers, my focus is always on authentic growth. I’m not a fan of manufactured numbers or obfuscated jargons and abbreviations. I’d much rather jump into a project and figure out how we can solve a problem in a way that actually makes sense for the long term.

Over the years, I’ve had the chance to be part of multiple startup acquisitions and corporate spinoffs, but what I enjoy most is working with passionate teams.

The Value I Bring:

  • Multidisciplinary Strategy: ability to talk product, data, finance, marketing, and sales.

  • Drives decisions with data: I build the Northstar dashboards—mapping onboarding funnels, revenue-to-behavior patterns, and cohort retention—that provide the data-driven thesis for growth.

  • Operational Agility: I specialize in improving in-flight processes and auditing customer friction points (like support backlogs) to eliminate the stumbling blocks that prevent long-term retention.

  • Early-Stage Execution: I’ve been a foundational hire for teams that scale and win, including:

    • Compose (YC W11) – Acquired by IBM
    • GradesFirst – Acquired by EAB
    • Crunchy Data – Acquired by Snowflake

I don’t just build features; I build the systems, data models, and processes that turn early-stage potential into enterprise-grade value.

Experience

Director of Product Strategy & Growth

Crunchy Data (acquired by Snowflake)
February 2022 - June 2025

Product Retention & Engagement Consultant

eMeals
August 2021 - January 2022

Product Strategy & Analytics I specialize in bridging the gap between raw customer data and actionable product roadmaps. My work focuses on building the infrastructure necessary to scale retention and streamline operations.

Metric Strategy: Defined and built Northstar dashboards to track the full user lifecycle—from Day 1 onboarding and funnel conversion to long-term cohort retention and revenue-to-behavior mapping.

Customer Advocacy: Conducted deep-dive audits of support backlogs, categorizing thousands of tickets to pinpoint friction points and bugs that were directly impacting churn.

Operational Excellence: Improved in-flight product processes by balancing aggressive growth goals with the organization’s specific risk tolerance for change.

Strategic Planning: Developed data-backed theses for product improvements, ensuring every engineering sprint moved the needle toward our long-term Northstar goals.

Entrepreneur in Residence

Techstars Energy Accelerator
August 2021 - December 2021

Founder

BuildPlane
October 2019 - February 2021

CTO and Strategic Business Advisor

Cloverly
March 2019 - October 2019

In 2019, launched Cloverly, an api-for-carbon-offsets from prototype to new product. Sketched out the platform and marketing plan. Designed and built the API and onboarding platforms. Launched the market plan based on an inbound-content strategy. Took product from 0 customers to 50 within 3 months. Top-6 on Product Hunt for Earth Day 2019.

Led product design of the Carbon Offset as an API platform. Built the tech stack on technologies that prioritized delivery speed and sub 20ms API performance: Ruby web / http engines (Rails + Grape) with Postgres as the database.

Manager

IBM Digital Business Group
December 2017 - January 2019

Led organizational change and product improve change through metrics. Led a team who worked directly with IBM product teams, with a goal of teaching those product teams to use data and metrics to think about improving their results.

Topics taught included:
- marketing campaign attribution
- product improvement through experimentation
- wholistic product usage customer experience (SEO, marketing, product, support)
- self-service funnel optimization
- financial projection through funnel understanding

Various Roles - 1st employee at startup

Compose (acquired by IBM)
December 2011 - June 2015

I was the 6th person at Compose. I performed the job that needed to be done from product engineering, support desk, conference presenter, sales, financial metrics support, and marketing. My diverse skill set worked well in the early days of a resource constrained company.

Product manager on PostgreSQL product launch, including:

  • product requirement spec creation, including:
    • minimize required human interaction
    • high-availability
    • automatic recovery of failed hosts
  • product project management
  • launch marketing and blog posts

Relied on metrics, funnel optimization practices, and SEO to improve trailing 30 day conversions by 262%

  • Created the funnel that was previously unknown, and applied metrics and funnel progress.
  • Uncovered and defined customer segments based on usage intention, and targeted customers with messaging based on those segments
  • Tools used:
  • Email drip campaigns
  • Home rolled metrics gathering system built
  • SEO & greenfield blog content generation
  • A/B tests
  • Regularly spoke at MongoDB conferences on database optimization and scaling

Database system sales, consulting, and implementations

  • Sold over $500,000 in ARR for database services
  • Optimized running MongoDB datasets using both indexes optimization and customer application change consultation
  • Implemented and migrated customers to the MongoHQ platform

As a team leader and programmer launched a new database UI and deployment platform

  • Lead daily standups with teams, and organized regular reporting
  • Used the following technologies:
  • Ruby & Rails
  • Javascript / Backbone.js
  • MongoDB / MySQL / Postgres / Redis

Process Optimization Engineer & Q/A

  • With targeted metrics and analysis, reduced the number of failures by 66%, which subsequently reduced support load by 20%

Director of Operations

GradesFirst (acquired by EAB)
June 2010 - January 2012
  • Revenue growth of over 500%
  • Growth from 49 to 181 colleges and universities

Product management

  • Created a virtuous cycle of feedback from customer support to product team
  • Conducted regular conversations with customers and prospects to match product-market needs
  • Programmed and launched features

Infrastructure scaling

  • Grew MySQL and Ruby on Rails infrastructure from single server to multi-server sharded environment
  • Maintained the infrastructure within budget

Team growth

  • lead the team as we grew from 8 employees to 20.
  • hired, trained, and managed employees in both junior and senior roles

Business Process Engineer

Harbert Management Corporation
February 2006 - June 2010

Increased the effectiveness of technology at a corporate level; managed projects for business process efficiency applications: CRM, Deal Flow, Change Management, and Document Creation

400x increase in client traffic to customer facing portal integrated with CRM SOA venture capital deal flow pipeline application

4x increase in efficiency of accounting process using collaborative application

Automated change management for auditable changes to accounting systems

Instituted and trained users on collaborate intranet sites

High School Teacher

Oxford City Schools
July 2004 - February 2006

While teaching young people, I learned:

  • Students want to learn.
  • Given a supportive environment, with proper tools, never underestimate a person's potential.
  • To expect a student to always be their best self was unrealistic; we don't know what happened the other 23 hours / day. But, they should achieve at least 90% of the time.

Education

University of Montevallo

BBA, Management
2000 - 2024

University of Alabama at Birmingham

MBA, Finance
2007 - 2009

Skills

Financial Analysis Process Management Product Development Project Management Ruby on Rails Start-ups