Building Cloudflare's Mid-Market Growth Engine
Security, network, and platform selling at scale—driving new logo acquisition and customer expansion across Territory accounts.
Strategic Focus
Mid-market leadership that scales teams with clear frameworks and repeatable plays
Team Building
15+ years building high-performing teams with 8+ AE promotions
Proven Results
107% attainment, #1 revenue teams, Presidents Club recognition
Agenda
A comprehensive overview of my approach to building Cloudflare's mid-market growth engine
About Me
Professional expertise meets personal passion
Strategic security & platform sales leader with 15+ years building high-performing teams at Okta and Cisco Meraki.
Led top-ranked teams (#1 revenue FY22; top-5 in FY23/FY24) through structured coaching using Challenger/Radical Candor methodologies. Built repeatable GTM programs and multi-team initiatives that drove pipeline and closed-won revenue.
Oakland resident with my wife and two sons (5 and 2.5).
Bringing the same discipline and teamwork from athletics to building world-class sales organizations.
Why Me for Cloudflare Mid-Market
I build high-performing mid-market teams that drive new logo acquisition and customer expansion through clear frameworks and repeatable plays.
I've managed 8+ AE teams driving new logo acquisition and expansion in the mid-market segment. At Cisco Meraki, I ran the #1 global Select team with a $75M book—exactly the scale and motion Cloudflare needs.
Deep experience selling complex security and network platforms to technical buyers (DevOps, SecOps, Infrastructure teams) and executive stakeholders—the exact multi-threaded approach Cloudflare requires.
Promoted 8 AEs through structured coaching frameworks (Challenger, Radical Candor) and transparent scorecards. Built repeatable enablement programs that consistently produce top-quartile performers.
Proven track record of accurate forecasting and pipeline management. 107% attainment with consistent quarterly commits through data-driven inspection rhythms and clear accountability.
At Okta, my teams consistently finished top-5 in revenue (37% YoY growth in H2FY26) and produced multiple promotions by running simple, repeatable cadences. At Cisco Meraki, I ran the #1 global Select team and a $75M book while helping build the mid-market motion from the ground up—the exact experience Cloudflare needs for Territory growth.
People Management
Building credibility, inspiring teams, and creating a recruiting engine that scales
Demonstrate Expertise
Highlight relevant experience from Okta and Cisco Meraki covering mid-market and enterprise. Share success stories and discuss strategies for their opportunities.
Be Vulnerable
Acknowledge areas where I need to get up to speed on Cloudflare's platform. Ask for feedback, insights, and perspectives. Immerse myself in training and ride-alongs.
Establish Mutual Respect
Recognize the team's tenure and experience. Ask questions to understand their current processes and challenges. Avoid coming across as knowing everything already.
Set a Positive, Energized Tone
Convey confidence and passion for Cloudflare while celebrating wins, successes, and fostering a supportive environment.
Align on Clear Goals and Accountability
Set clear expectations immediately. Implement tracking and accountability. Agree upon specific achievable metrics.
Focus on Continuous Improvement
Provide coaching and constructive feedback. Encourage knowledge sharing and utilizing cross-functional teams.
Lead by Example
Model behaviors and work ethic you expect to see. Be a constant student of technology and remain involved daily without exception.
Build a Diverse, High-Potential Team
Focus on individuals who are process-oriented, have grit, are coachable, and constantly searching to improve. "Always improving" (inside or outside of work) is my highest priority—this characteristic consistently represents the hardest working and highest potential individuals.
Maintain a Continuous Pipeline
Always be interviewing. Build relationships with high performers in adjacent segments and maintain a funnel of candidates. Work with recruiting partners to identify star talent early.
Hire for Cloudflare's Technical Selling Motion
Prioritize candidates with experience selling to technical buyers (DevOps, SecOps, Infrastructure teams) and those comfortable with PLG motions. Look for multi-threading ability and comfort navigating complex organizations.
Key Hiring Criteria
My expectations are broken down into three clear areas: Numbers, Behavior, and Activities. While I'm not a micromanager, I believe in the "trust but verify" model—everyone needs accountability.
Numbers
- Quota Attainment
- YoY Growth
- Pipeline Generation
Behavior
- Punctuality
- Attitude & Respect
- External Engagement
- Professionalism
Activities
- Calls & Emails
- Demos & Trials
- Customer Meetings
- SFDC Hygiene
Coaching Process
If two of three areas are being met satisfactorily, I have one area to coach. If two of three areas are not being met, I pursue documented coaching:
- 1.1 full quarter of direct feedback and coaching with active monitoring
- 2.1-2 months of documented coaching if results aren't obtained
- 3.1 month PIP as final step
Business Management
Cross-functional alignment, partner-first mindset, and executive engagement strategies
Success at Cloudflare requires tight alignment across multiple teams. I'll establish recurring sync points with key stakeholders to drive coordinated execution.
Partners
Bi-weekly syncs with partner team to identify co-sell opportunities and align on PowerUP program initiatives.
Partner-First MindsetMarketing
Collaborate on campaigns, events, and ABM plays. Leverage Cloudflare's technical content and developer community.
Campaign AlignmentBDRs
Weekly pipeline reviews and account planning. Align on target accounts and messaging for outbound motions.
Pipeline GenerationSales Engineers
Bi-weekly technical enablement and deal strategy sessions. Ensure AEs understand Cloudflare's platform capabilities.
Technical EnablementHR & Recruiting
Monthly talent pipeline reviews. Maintain continuous recruiting motion and career development plans.
Talent PipelineSales Ops
Weekly forecast reviews and data analysis. Leverage insights to optimize territory coverage and resource allocation.
Data-Driven DecisionsCloudflare's PowerUP Partner Program offers significant opportunity for mid-market growth. I'll drive a partner-first approach across the team.
Activate Local VAR Ecosystem
Build relationships with regional VARs and system integrators who have existing relationships with target accounts. Create joint account plans and co-selling motions.
Leverage Solution Bundles
Train AEs on Cloudflare's partner solution bundles for SASE and application services. Make partner engagement a standard part of deal strategy.
Partner-Sourced Pipeline
Establish KPIs around partner-sourced and partner-influenced pipeline. Recognize and reward AEs who effectively leverage the partner ecosystem.
Joint Business Planning
Conduct quarterly business reviews with top partners. Align on target accounts, vertical strategies, and co-marketing initiatives.
Mid-market deals require face-to-face engagement. I'll establish clear expectations around field presence and customer meetings.
In-Territory Expectation
AEs should be in-territory regularly for customer meetings, partner events, and local networking. Face-to-face builds trust and accelerates deals.
Customer Events
Host quarterly customer events (dinners, roundtables, technical workshops) to build relationships and generate pipeline. These consistently deliver 4x ROI.
Executive Engagement
For strategic accounts, facilitate executive-to-executive engagement. Bring in Cloudflare leadership for key meetings and QBRs.
Establish Executive Outreach and Alignment
For accounts with $50k+ potential, AEs must develop relationships beyond their day-to-day technical contacts. This means engaging CTO, VP Engineering, CISO, and other executive stakeholders.
Map the Organization
Understand reporting structures, decision-makers, and influencers across Security, Network, Development, and Infrastructure teams.
Executive Sponsorship
Identify and cultivate executive sponsors who can champion Cloudflare internally and navigate procurement processes.
Remain Multi-Threaded
Single-threaded deals are high-risk. AEs must maintain relationships across multiple personas and departments to de-risk deals and uncover expansion opportunities.
Key Personas for Cloudflare
Customer Executive Connect (CEC) Program
Leverage Cloudflare's executive team for strategic account engagement. Schedule CEC sessions for high-value opportunities to demonstrate commitment and align on business outcomes. These sessions accelerate deal velocity and increase win rates.
I'm a believer in repeatable processes that never waver. Managers and sellers want a leader who is the rock—never falters and leads the charge. These recurring meetings take priority.
Team Cadences
- Weekly 1:1s with each AE
- Weekly team meetings
- Bi-weekly Gong call reviews
- Monthly pipeline reviews
- Quarterly QBRs
Cross-Functional Cadences
- Bi-weekly Marketing sync
- Bi-weekly SE Manager sync
- Bi-weekly BDR Manager sync
- Bi-weekly Partner org sync
- Monthly HR/Recruiting sync
Revenue Management
Operating rhythm, KPIs, and strategies to scale Cloudflare's mid-market revenue
Clear metrics and inspection rhythms drive accountability and predictable revenue growth. I'll establish data-driven KPIs aligned with Cloudflare's mid-market motion.
New Logo Acquisition
- New accounts closed
- Average deal size
- Sales cycle length
- Win rate by segment
Expansion & Retention
- Net revenue retention
- Product attach rate
- Expansion ARR
- Churn risk accounts
Pipeline Health
- Pipeline coverage (3-4x)
- Pipeline generation
- Stage progression velocity
- Forecast accuracy
Activity Metrics
- Customer meetings
- Demos & trials
- Partner engagement
- SFDC hygiene score
Weekly Inspection Rhythm
Monday: Pipeline Review
Review commit forecast, stage progression, and at-risk deals. Identify where to focus resources.
Wednesday: Deal Strategy
Deep-dive on $50k+ opportunities. Multi-threading, competitive positioning, and close plans.
Thursday: Activity & Coaching
Review activity metrics, Gong calls, and provide real-time coaching on customer interactions.
Friday: Pipeline Generation
Focus on top-of-funnel activities, partner sourcing, and next week's customer meetings.
For opportunities $50k and above, I'll be directly involved in deal strategy, customer engagement, and close planning. This ensures we're maximizing win rates on high-value deals.
Deal Strategy Sessions
Weekly reviews of large opportunities. Assess competitive landscape, validate multi-threading, and ensure we have executive sponsorship.
Customer Engagement
Join key customer meetings to build relationships, demonstrate commitment, and help navigate complex organizational dynamics.
Close Planning
Develop mutual close plans with clear milestones, stakeholder alignment, and risk mitigation strategies for every large deal.
Where Are the Large Deals?
I'll work with Sales Ops and the team to identify accounts with the highest revenue potential based on company size, tech stack, and current Cloudflare usage.
Platform Consolidation Plays
Target accounts using multiple point solutions (Zscaler, Akamai, legacy WAF/CDN) that can consolidate onto Cloudflare's unified platform.
Zero Trust Migrations
Companies moving from VPN to Zero Trust architecture. Cloudflare One (ZTNA, SWG, CASB) is a natural fit for mid-market.
Developer Platform Adoption
Digital-native companies building on Cloudflare Workers. Land with developers, expand to enterprise security and network services.
Multi-Product Expansion
Existing customers using 1-2 products. Identify opportunities to expand into Email Security, DLP, Magic WAN, or application services.
Top Accounts Strategy
Identify the top 20% of accounts that will drive 80% of revenue. Build comprehensive account plans with clear stakeholder maps, product roadmaps, and executive engagement strategies.
While pursuing large strategic deals, we need quick wins to build momentum and confidence. I'll identify easy expansion opportunities and fast-close scenarios.
Product Attach Plays
Identify customers using CDN/WAF who haven't adopted Email Security, DLP, or CASB. These are natural expansions with short sales cycles.
30-45 Day CloseTrial Conversions
Leverage Cloudflare's PLG motion. Identify accounts with active trials or free-tier usage and convert them to paid enterprise plans.
15-30 Day CloseEarly Renewal Upsells
Contact customers 9-12 months before renewal. Bundle additional products and lock in multi-year commitments with early renewal incentives.
60-90 Day CloseRetention is revenue. I'll implement early warning systems and proactive engagement strategies to identify and mitigate churn risk before it's too late.
Early Warning Indicators
- Declining product usage or engagement metrics
- Executive sponsor turnover or organizational changes
- Support ticket volume or escalations increasing
- Lack of engagement (no meetings in 60+ days)
- Competitive activity or RFP requests
Proactive Mitigation Strategies
- Quarterly business reviews with all at-risk accounts
- Executive engagement and CEC sessions to rebuild relationships
- Product adoption workshops and technical enablement
- Introduce new products/features that solve emerging pain points
- Early renewal conversations with incentives (9-12 months out)
Churn Prevention is a Team Sport
Work closely with Customer Success, Support, and Product teams to identify at-risk accounts early. Establish a weekly churn risk review and assign clear ownership for mitigation plans.
Vertical-Specific Plays
Work with Marketing and Product to identify high-growth verticals (SaaS, FinTech, E-commerce) and develop tailored messaging and use cases for each segment.
Event-Driven Pipeline
Leverage Cloudflare events (Cloudflare Connect, regional meetups) and industry conferences to generate pipeline. Host quarterly customer dinners and technical workshops.
Competitive Displacement
Build targeted plays against Zscaler, Akamai, and legacy security vendors. Train AEs on competitive positioning and TCO analysis for platform consolidation.
Data-Driven Territory Planning
Use Sales Ops data to identify whitespace, optimize territory coverage, and ensure AEs are focused on highest-potential accounts. Rebalance territories quarterly.
30/60/90 Day Plan
Enterprise & security-specific roadmap for immediate impact
- 1:1s with all team members
- Establish clear expectations and scorecard
- Start weekly Gong review rotation
- Map AEs/SEs/Partner managers relationships
- Set recurring cross-functional cadence
- Stand up Marketplace co-sell path
- Identify top-25 accounts by security signal
- Launch fast-start plays for easiest cross-sell
- Queue larger whale opportunities
- MEDDIC/Command of the Message refresh
- Align to each pillar talk track
- Product-specific coaching sessions
- Host first Customer Executive Council
- Run Code→Cloud On-Site sprint weeks
- Launch first partner roadshow
- Publish "Top 10 security plays" board
- Set attach-rate targets by pillar
- Establish pipeline inspection rhythm
- Institutionalize quarterly QBRs
- Establish Pipeline Deep Dive process
- Launch promotion paths and recognition
- Analyze conversion and cycle time
- Review partner-sourced mix
- Tune resourcing (overlay ratio, SE hours)
- Publish first Labs-powered research briefing
- Connect research to customer opportunities
- Establish thought leadership pipeline
Success Metrics
Team aligned, processes established, quick wins identified
Field motion launched, pipeline building, enablement complete
Scalable systems, optimized performance, thought leadership active
Proof & Recognition
Credible track record of building high-performing teams and driving enterprise revenue
Key Achievements
Program Leadership
Key Achievements
Program Leadership
Consistent Excellence: Multiple years of top-quartile performance, team leadership recognition, and measurable impact on organizational growth through repeatable programs and structured coaching methodologies.
Let's Build Together
Ready to discuss how I can help build Datadog's enterprise security growth engine?
cody.snay@gmail.com
Phone
805.268.5142
Location
Oakland, CA
"I'm excited to bring my proven track record of building enterprise security teams to help Datadog capture the massive market opportunity ahead."
- Cody Snay