Ryan Caballero

Account Executive (West Coast/San Francisco)

Infisical

Account ExecutiveBalancedConsultative📍 San Francisco, CA or New York, NY
Deal Size: $50-200K ACV
Sales Cycle: 4-8 weeks (startups), 3-6 months (enterprise)
Posted by Ryan Caballero

Overview

You're selling Infisical's secrets management platform to DevOps engineers, platform teams, and security buyers. Half your deals are with fast-growing startups who need to get off manual secret management quickly ($50-100K ACV), and half are enterprise organizations with complex compliance requirements ($200K+ ACV). You're competing against HashiCorp Vault, AWS Secrets Manager, and Azure Key Vault.


Role Snapshot

AspectDetails
Role TypeFull-cycle AE (prospect to close)
Sales MotionBalanced - mix of inbound PLG conversions and outbound to security teams
Deal ComplexitySplit between consultative (startups) and enterprise (large orgs)
Sales Cycle4-8 weeks (startups), 3-6 months (enterprise)
Deal Size$50-200K ACV (split across both segments)
Quota (est.)$750K-1M/year

Company Context

Stage: Likely Series A/B (28 employees, selling to NVIDIA and LG suggests meaningful traction)

Size: 28 employees

Growth: Hiring both coasts simultaneously, customer list includes high-profile names

Market Position: Challenger in crowded secrets management space against HashiCorp Vault (market leader), cloud-native options (AWS/Azure/GCP), and newer entrants


GTM Reality

Pipeline Sources:

  • 40% Inbound - developers who discover Infisical through open-source version, GitHub, or developer communities. Quality varies widely from tire-kickers to teams ready to buy.
  • 40% Outbound - you're targeting platform engineering teams at Series B+ startups and security teams at enterprises. Cold outreach to DevOps/security leaders.
  • 20% Product-Led - teams using free/OSS version who need enterprise features (RBAC, audit logs, compliance controls)

SDR/AE Structure: At 28 people, likely 1-2 SDRs max or you're doing your own prospecting

SE Support: Founders/technical team helps on enterprise deals; you handle technical conversations on SMB deals


Competitive Landscape

Main Competitors:

  • HashiCorp Vault (market leader, complex but trusted)
  • AWS Secrets Manager, Azure Key Vault, GCP Secret Manager (cloud-native, good enough for many)
  • Doppler, Akeyless (newer challengers)

How They Differentiate: All-in-one platform (secrets + certificates + PAM vs point solutions), modern UX vs Vault's complexity, multi-cloud vs cloud-specific tools

Common Objections:

  • "We're already using [AWS/Azure/Vault]"
  • "Our security team won't approve a smaller vendor"
  • "We built something internal already"
  • "We're not sure we need all these features"

Win Themes: Easier to use than Vault, better visibility/control than cloud provider tools, unified platform vs managing multiple tools


What You'll Actually Do

Time Breakdown

Prospecting (30%) | Active Deals (45%) | Internal (25%)

Key Activities

  • Outbound to platform teams: You're cold-calling/emailing VPs of Engineering, DevOps managers, and security leaders at Series B-D startups. Most ignore you. You're trying to find teams who've had a secrets leak or are hitting limits with their current tool.
  • Converting PLG users: Developers sign up for the open-source version. You're identifying which ones work at companies big enough to pay, then trying to get them to bring in their manager for an enterprise conversation. Many are just exploring.
  • Running technical demos: Startup deals, you do the demo yourself (show integrations, explain RBAC, walk through migration). Enterprise deals, you bring in founders or technical team for deeper architecture discussions.
  • Navigating enterprise procurement: For large deals (LG, NVIDIA, Marsh), you're dealing with security reviews, vendor questionnaires, procurement processes, legal negotiations. Lots of waiting on committees.

The Honest Reality

What's Hard

  • You're selling two completely different motions simultaneously. Startup deals move fast but are price-sensitive. Enterprise deals are bigger but take 4-6 months and involve security reviews you may not pass (you're 28 people competing against HashiCorp).
  • Most inbound leads are developers who want free stuff or are just comparing options. Converting them requires finding economic buyers (their managers) who often don't know their team is using you.
  • "We already have something that works" is the default state. You're fighting inertia and switching costs, not just competitors.
  • At this stage, product gaps exist. Prospects will ask for features you don't have yet. You're selling roadmap often.
  • Enterprise security teams are skeptical of smaller vendors. You'll lose deals purely on vendor risk concerns.

What Success Looks Like

  • Closing 2-3 deals per quarter: one enterprise ($150-250K), two startups ($50-100K each)
  • Building a pipeline where 40% is enterprise (slow but big) and 60% is SMB/mid-market (faster velocity)
  • Getting comfortable saying "we don't have that yet but here's our roadmap" without losing the deal

Who You're Selling To

Primary Buyers:

  • VP Engineering / Head of DevOps (startups) - cares about developer productivity, reducing incidents
  • CISO / Director of Security (enterprise) - cares about compliance, audit trails, risk reduction
  • Platform Engineering leads - cares about consolidating tools, improving secrets sprawl

What They Care About:

  • Preventing secrets leaks (every company has had a close call or actual incident)
  • Audit trails and compliance (SOC2, HIPAA, FedRAMP requirements)
  • Developer experience (will engineers actually use this vs workarounds?)
  • Migration complexity (how hard to switch from current solution?)
  • Vendor stability (are you going to be around in 3 years?)

Requirements

  • 2-4 years selling technical infrastructure software (security, DevOps tools, cloud infrastructure)
  • Comfortable having technical conversations with engineers (understand CI/CD, Kubernetes, cloud providers)
  • Experience managing both transactional and enterprise sales cycles
  • Self-starter mentality - at 28 people, there's no massive playbook or support team
  • Located in or willing to relocate to San Francisco Bay Area