"Navigating diverse environments has taught me that adaptability is the ultimate superpower. This mindset shapes how I solve complex challenges—with resilience, creativity, and precision."
Hello! I'm Diego.I help bold companies scale revenue operations and growth.

I specialize in building revenue processes from scratch, designing effective compensation plans, and scaling operations to deliver transformative results. With a proven track record of scaling businesses from early-stage ventures to $100M+ ARR, I create systems that drive both immediate impact and sustainable growth.
While my expertise spans fitness, healthcare, behavioral health, and HR tech, I bring highly transferable skills to drive growth across any industry.
What People Say About Me
"Throughout my tenure as Headways Salesforce Account Executive - I engaged in strategic collaboration with Diego, across various initiatives such as RevOps and the establishment of top-tier sales and service teams at Headway. Diego is a natural leader who brings robust technical expertise with a keen business acumen. Diego's remarkable skill in zooming out to comprehend the broader implications and downstream effects of digital transformation, all while maintaining a sharp focus on specific high-priority elements, was truly impressive."
Alexander Matarazzo
Enterprise Banking Sales - Salesforce
"I am truly lucky to have had the opportunity to learn and grow under Diego's leadership during his time at Headway. His role in scaling our revenue operations team was critical in supporting Headway's early stage growth and cannot be understated. As the first revenue operations hire, he led critical initiatives that helped build the foundation of our GTM infrastructure. His strategic insights and ability to motivate his reports to deliver their best work enabled our team to make a huge impact across our cross functional partners in sales, marketing, and customer success."
Jerome Rigor
Revenue Operations at Headway
"I had the pleasure of working closely with Diego as his direct report in my role at Headway. Diego is an exceptional leader and an expert in taking initiatives from zero to one. His knowledge spans a wide range and his ability to navigate complex challenges is truly impressive. Diego played a pivotal role in establishing and growing the Revenue Operations team at Headway. Without his tireless effort and leadership, our team wouldn't be where it is today."
Eric Black
Revenue Operations Lead at Headway
"Diego is an experienced Revenue Operations leader that would be an asset to any team. Diego was the founding member of the RevOps team at Headway and wore many hats, including but not limited to compensation planning and calculations, sales process design, system implementations, and strategic projects to increase lead flow and revenue. Diego is also an exceedingly supportive manager who always looks out for his team, and anyone who gets to report to him should consider themselves lucky!"
Allie Ryu
RevOps & GTM Systems Expert
"I have worked closely with Diego for the past year at Kaia Health and know first hand, the value of his contributions. Diego combines his passion for helping others and enthusiasm with his ability to engage cross-functional teams, which leads to meaningful change on any project he's leading. Diego's positive attitude and approach to challenges is an incredible asset, as every winning team needs an individual like Diego to push others to overcome adversity."
Josh Koch
Business Development Leader | Growth Accelerator | Mission-Driven
"Diego is an exceptional colleague. Not only does he have a positive and collaborative attitude at all times, but he is a creative problem solver that keeps the company mission alive for all. Diego's work is dependable, consistently accurate and evolving, and his focus on process improvement does not go unnoticed by anyone at Kaia."
Jessica Cooper
Driving Growth in Healthcare Tech
"I have worked closely with Diego at Kaia for the past year and a half at the time of writing. Professionally, Diego is a meticulous operator who approaches objectives analytically and thoroughly. From a quality of work and productivity angle, I would recommend Diego strongly and am delighted to be his colleague. Personally, Diego is a warm and thoughtful collaborator, always putting the wellbeing of others ahead of himself. As well as a colleague, I can call him a good friend, and those who work with him feel the same. Diego would be an asset to any team he joins from both perspectives."
Mark Liber
Helping community organizations improve community health
Experience

Founder
Climb Consulting · New York, NY
- Enabled $75M in aggregate client funding by developing growth frameworks that improved scalability and market positioning for health tech and HR startups
- Generated 100K+ leads and drove 300+ strategic meetings by managing targeted email outbound campaigns and leveraging data-driven prospecting tools
- Implemented CRM systems (HubSpot, Apollo.io) and data enrichment tools to automate lead workflows, enhance analytics, and improve sales pipeline efficiency

Founder and Advisor
Refined Vida · Miami, FL
- Achieved 25% monthly client growth by launching personalized wellness programs tailored to individual needs
- Designed a compensation model tied to business and health outcomes, ensuring timely payouts and effective incentives
- Recruited and trained 8+ providers (MDs, NPs, RNs), maintaining a 90% retention rate and consistent 5-star client satisfaction
- Transitioned to an advisory role in Sep 2024, focusing on strategic guidance and brand positioning

Revenue Operations Manager
Headway · New York, NY
- Scaled the provider network from 800 (NY) to 25,000 nationwide, driving ARR growth from $5M to $100M+ by leading Revenue Operations for a 180+ member Growth Team
- Built automated dashboards in Salesforce, Outreach, and Google Sheets to track performance and compensation, achieving 60%+ quota attainment across the sales team
- Led integrations of Marketo, LeanData, Outreach, and Salesforce, reducing lead leakage by 10–20% and ensuring <5 min outreach for 99% of submissions
- Managed a $200K Salesforce redesign and a $1M annual tech stack budget while building and leading a team of 4 (1 lead, 2 senior associates, 1 Salesforce admin)
- Collaborated cross-functionally on incentives, OKR alignment, SPIFs, PIPs, accelerators, and recognition programs to drive team performance and retention

Marketing, Sales and Operations Manager
Kaia Health · New York, NY
- Managed a centralized, automated lead generation motion that generated a $10M pipeline and established early market traction
- Transitioned CRM to HubSpot, improving pipeline visibility and reporting accuracy for employer sales
- Led weekly pipeline reviews and sales calls, creating a structured cadence to drive sales performance
- Coordinated content strategy with writers to align messaging and support employer sales initiatives

B2B Operations Intern
Gympass (Wellhub) · New York, NY
- Supported US market expansion through sales engineering support
- Developed data visualizations using Tableau for client engagement
- Conducted data analysis to optimize client engagement strategies
- Assisted in process optimization for operational efficiency
Education

B.S. in Business Administration
University of Southern California · Los Angeles, CA
Licenses & Certifications
Portfolio
Areas of Expertise
Driving Sales Efficiency with Data Visualization
Reduced enterprise sales cycles by 2-3 months through data-driven demonstrations
Building Outbound Sales Infrastructure
Built comprehensive outbound infrastructure driving $100K+ pipeline and supporting $80M funding
Outbound Sales and CRM Optimization
Generated $50M+ pipeline through optimized outbound sales and CRM processes
Scaling MSK Solutions for Fortune 500s
Generated $10M pipeline and secured strategic partnerships through streamlined operations
Eliminating Bottlenecks in Sales Processes
Reduced manual data errors by 90% and improved quota payout accuracy by 95% through Salesforce optimization
Building and Scaling the RevOps Team
Scaled RevOps team to support 180-member growth team and $100M ARR
Revenue Recognition Alignment
Streamlined revenue recognition process and improved sales motion visibility
Email Infrastructure for Scale
Built robust email infrastructure achieving 60%+ open rates for 30K-40K monthly emails
Scalable Onboarding Process
Increased post-onboarding appointments by 20% through automated provider onboarding
Streamlining Operational Support
Achieved 95% SLA compliance and improved team satisfaction through streamlined operational support
Resolving Stakeholder Priorities and Driving Alignment
Successfully transitioned team to Salesforce and implemented revenue-linked KPIs
Enhancing Forecasting and Sales Motion Segmentation
Increased rep efficiency by 30% through improved forecasting and sales motion segmentation
Competitor Takeout Project
Transformed outbound operations achieving 60% competitor market share capture