AeroLeads people directory · profile
Rob Headley Email & Phone Number
Head of Enterprise Sales
at
incident.io
1 work email found
@cloudflare.com
LinkedIn matched
✓ Verified July 2026
4 data sources
Profile completeness 100%
Current company
Role
Head of Enterprise Sales
Location
San Diego, California, United States
Who is Rob Headley? Overview
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Quick answer
Rob Headley is listed as Head of Enterprise Sales at incident.io, based in San Diego, California, United States. AeroLeads shows a work email signal at cloudflare.com and a matched LinkedIn profile for Rob Headley.
Rob Headley previously worked as Executive Member at Pavilion and Health and well-being at Career Break. Rob Headley holds B.A., Economics from Ucla.
Company email context
Email format at incident.io
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{first_initial}{last}@cloudflare.com
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AeroLeads found 1 current-domain work email signal for Rob Headley. Compare company email patterns before reaching out.
Profile bio
About Rob Headley
Rob Headley is a Head of Enterprise Sales at incident.io. He possess expertise in seo, digital marketing, lead generation, sales, entrepreneurship and 45 more skills. He is proficient in Spanish. Colleagues describe him as "I have had the pleasure of working with Rob as we evaluated the usage of Cloudflare while I worked as a Security Architecture Analyst at Uptake. Rob made sure that we were supported for success every step of the procurement process in a positive, courteous, and professional sales manner. I have only good things to say about Rob and am very thrilled that working with him and Cloudflare has been so smooth!", "I have been setup for success by Rob, during the past several year, as I have lead transformational efforts here at Orvis. Having Rob's support and understanding of my organizational needs is a priceless asset and there is not a higher compliment that I could extend.", and "I have had the pleasure of working alongside Rob at BrightEdge. He is a driven, passionate and proven sales professional. He unselfishly shared best practices and has a level-headed attitude that brings the team back to balance no matter what the situation. I would highly recommend Rob for any position as he naturally accomplishes anything that he puts his mind to."
Listed skills include Seo, Digital Marketing, Lead Generation, Sales, and 46 others.
Current workplace
Rob Headley's current company
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9 roles
Rob Headley work experience
A career timeline built from the work history available for this profile.
Executive Member
Current
Sep 2024 - Present
Health And Well-Being
Career Break
After helping Cloudflare grow from <$100M to $1.3B+ over the past 8 years, I took some time to recharge, travel, and build new skills before my next leadership role.Over the past 6 months, I’ve reconnected with friends, spent quality time with family, built a consistent fitness routine, and made incredible memories exploring Europe and the Utah/Arizona backcountry with my wife.I also took a first-principles approach to learning AI, diving into the math and Python fundamentals behind how it all works. Now, I'm continuing to explore how agentic workflows can empower lean revenue teams as I search for a new leadership role. With a fresh perspective, I’m fully recharged and excited to help lead GTM at an innovative, high-growth company.
Feb 2024 - Aug 2024
Director Of Sales
2nd line leader responsible for overall GTM strategy and operations for a new mid-market segment focused on acquiring high growth digital native customers. 3 Front Line Sales Managers, 19 AEs, 6 BDRs.Focused on new business and expansion through a combination of PLG, outbound, and channel motions. Deal sizes ranging from $40k to over $1m with sales cycles ranging from 1 to 6 months, often with complex requirements and requiring C-level sponsorship Top performing Director of Sales in the Mid-Market organization in Q4 2022, Q1 2023, and FY2023 (#1 of 3 in quota attainment)Designed and owned the continuous optimization of the outbound sales model which was standardized for 100+ mid-market AEs and BDRs across North AmericaBuilt and optimized the Mid-Market deal qualification scorecard using a combination of MEDDPICC and value selling frameworksDesigned customizable pricing model for high compute AI customers resulting in turnkey expansion for key high growth customers Closed largest mid-market deal in 2022 and largest expansion deal with same AI customer in 2023, growing ARR nearly 5x
Jun 2022 - Jan 2024
Senior Sales Manager
Front line sales manager leading team of seven Account Executives focused on new business in North America. Highest performing team in 2019 and 2021Closed $15.9M in ARR and achieved 115% in average team quota performance over 14 quarters
Oct 2018 - Jun 2022
Enterprise Account Executive
Closed first $1M+ ARR customer for new SaaS focused product launched in 2017Q2 2018: #1 AE (Global)Q3 2018: #1 AE (North America)FY 2018: #2 AE (North America)
Jan 2016 - Oct 2018
Enterprise Account Executive
2nd US employee and 1st US sales hire for Series A marketing technology startupResponsible for US GTM strategy and operations. Reported directly to COO. Worked closely with C-suite in Tokyo to localize product for the US, find product/market fit and define ICP, manage pipeline operations, hire/lead inside sales development team, and acquire first US customers. I helped open the SF office, assemble the desks and chairs, and made the company’s very first cold call. The lessons I learned and mentorship I gained from our COO and SVP Sales along the way taught me how to embrace ambiguity and develop a builder mentality that fueled my success early on at Cloudflare.
Aug 2014 - Oct 2015
Enterprise Account Executive
Closed 27 deals ($675k ARR) with $250k in first 6 months on ramp. Finished Q1 2014 at 108% to goal (first fully ramped quarter)
Jul 2013 - Aug 2014
Enterprise Business Representative
Where I cut my teeth into SaaS sales and learned how to build my own pipeline. 110% quota attainment.
Jun 2012 - Jul 2013
2 education records
Rob Headley education
B.A., Economics
Ucla
Education record
Universitat Pompeu Fabra
FAQ
Frequently asked questions about Rob Headley
Quick answers generated from the profile data available on this page.
What company does Rob Headley work for?
Rob Headley works for incident.io.
What is Rob Headley's role at incident.io?
Rob Headley is listed as Head of Enterprise Sales at incident.io.
What is Rob Headley's email address?
AeroLeads has found 1 work email signal at @cloudflare.com for Rob Headley at incident.io.
Where is Rob Headley based?
Rob Headley is based in San Diego, California, United States while working with incident.io.
What companies has Rob Headley worked for?
Rob Headley has worked for Incident.Io, Pavilion, Career Break, Cloudflare, and Kaizen Ad.
How can I contact Rob Headley?
You can use AeroLeads to view verified contact signals for Rob Headley at incident.io, including work email, phone, and LinkedIn data when available.
What schools did Rob Headley attend?
Rob Headley holds B.A., Economics from Ucla.
What skills is Rob Headley known for?
Rob Headley is listed with skills including Seo, Digital Marketing, Lead Generation, Sales, Entrepreneurship, Cold Calling, Marketing, and Social Networking.
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