Drew Wasson
Strategic Operations Leader
Houston, TX · Remote / Hybrid / On-site · Full-time or Fractional
The operator who turns chaos into systems — and the right-hand the C-suite relies on to keep it that way.
Areas of Focus
Technology strategy and enterprise application portfolio leadership
By the Numbers
$250K+
annual cost removed through delivery model redesign
Crawford Consulting · Efficiency
100+ hrs/yr
manual work eliminated via AI & automation
Alert Logic · Efficiency
60+
concurrent projects governed under one PMO framework
Alert Logic · Scale & Impact
96%
NPS improvement across a 4,000+ account portfolio
Fortra · Scale & Impact
Overview
How the Work Gets Done
Core Operating Philosophy
- 1.
Understand the vision of success and the why.
- 2.
Identify what must be true to achieve the vision.
- 3.
Listen and map the reality.
- 4.
Establish the governance structure.
- 5.
Build relationships, bridge gaps, and solve problems.
Areas of Expertise
Operating Disciplines
Strategic planning, program/portfolio governance, OKR frameworks, M&A integration, change management, vendor & risk management, budget ownership ($2M departmental), solution architecture
Systems
CRM (Salesforce, Dynamics 365), ERP (SAP, Oracle, Infor), ITSM (Zendesk, Freshdesk), HRIS/ATS, SharePoint
Analysis
SQL, Power BI, AWS Redshift
AI & Automation
Claude, ChatGPT, AgentForce, RPA, Zapier, Power Automate
Experience
2011 – Present
Feb 2025 – Feb 2026
Director of Operations
Crawford Consulting
Founder-led B2B software company
- Built a greenfield GTM systems stack (Salesforce, AgentForce, ZoomInfo) from discovery to go-live in under 4 months, creating pipeline visibility across 40+ enterprise opportunities.
- Restructured delivery and staffing model, removing $250K in annual cost.
- Selected a PEO to stand up benefits administration from scratch and built an automated vacation tracking and approval workflow to replace manual recordkeeping.
- Rebuilt a $20B energy client relationship through executive and tactical communication cadences, protecting license and maintenance ARR and earning recognition that opened expansion opportunities.
Jun 2022 – Sep 2024
Principal Program Manager (Associate Director)
Fortra
Acquired Alert Logic in 2022 · 2,500+ employees · $800M+ revenue
- Increased NPS 96% via automated survey infrastructure across a 4,000+ account portfolio.
- 8+ years as product owner of enterprise ITSM platform (Zendesk), scaling to 600+ employees and 17,000 customers; selected as Zendesk customer speaker across 6 webinars and panels.
Mar 2015 – Jun 2022
Director of Information Systems / Director of Business Applications
Alert Logic
600+ employees · $140M+ ARR · acquired by Fortra
- Built a PMO governance framework with CFO sponsorship spanning 60+ concurrent projects across three competing business units.
- Designed a cross-functional release readiness framework, cutting new-release support tickets ~25%.
Mar 2014 – Feb 2015
Director, Business Applications
Express Energy Services
1,700 employees · $375M revenue
Jan 2011 – Mar 2014
Business Applications Architect
Flexsteel Pipeline Technologies
200+ employees · $100M+ revenue
Earlier
Lead Consultant · Sr. Business Systems Analyst · Management Consultant
BizAps
Hewlett-Packard
PwC / IBM Business Consulting Services
Things I've Built
Systems, Not Just Roles
NWAL Scheduling App
AI-assisted scheduling tool for youth swim meets — helps meet referees schedule officials on deck.
- Production pilot for the 2026 JVS season
- Team-balancing logic and capability cascade enforcement
- XLSX export and admin dashboard
- Real-meet bugs identified and resolved during live use
College Tracker
Full-stack tool for managing college applications — deadlines, essays, accomplishments, recommenders, and scholarships.
- Role-based permissions enforced at the database layer (owner / parent-editor / read-only)
- Built in response to real gaps in existing tools like MaiaLearning
Out of the Office
Advisory & Community Leadership
City Council Member, Jersey Village, TX
May 2019 – May 2026City of 8,000 residents. 4 consecutive terms. Oversaw $70M+ annual municipal budget, 2 enterprise funds, 2 special districts, and a 10-year capital improvements plan.
Board Member, Senate Avenue Brewing Company
Senate Avenue Brewing Company is a profitable 7-figure restaurant and micro-brewery in Jersey Village, Texas. Since 2021, counseling on operational strategy and growth while establishing the governance framework for owner distributions.
Swimming Official
Since 2021, volunteer for youth swim team (NWAL) and high school (UIL). Built an AI-assisted scheduling tool that helps meet referees assign officials on deck.
Houston Livestock Show and Rodeo
Committee volunteer for 15+ years. Scholarship Administration Committee. HLS&R has funded more than $660m to youth and education since 1932.
13-Time Marathon Finisher
Texas A&M University
B.S. Journalism · minor, Business Administration · magna cum laude
Featured Thinking
How I See the Work
01 / 07
Choose Your Hard
Testimonials
What People Say
“Drew is action-oriented, process-driven, and a terrific teammate... Drew is a positive addition to any organization.”
“Drew would be a great fit in any organization looking for a leader who can operate in complexity, earn trust across a diverse set of stakeholders, and bring order to ambiguous situations.”
“The scheduling tool you developed is AMAZING! This is a game changer.”
“You can't go wrong if you have a Drew in your corner. That's a fact!”
Contact
Let's Talk About How Can I Help You
Houston-based and open to remote, hybrid, or on-site roles. Considering full-time and contract / fractional engagements.
If you're building something and need help with operations, governance, or systems, let's talk.
Connect on LinkedIn