Checkly empowers developers and agents to own and ensure application performance and reliability, from pull request to post-mortem
Tony Merlino, Chief Revenue Officer, shares details on Checkly’s Sales org, and what its like to work there.
In This Video:
Overview of Checkly
Checkly is a remote-first startup founded in 2020 operating in the synthetic monitoring and observability space. The company bridges the gap between testing and monitoring using a headless platform built specifically for developers and AI agents. Checkly helps engineering teams detect incidents, communicate issues to stakeholders, and resolve performance problems before end users are impacted. Checkly raised a $20 million Series B funding round in July 2024 to accelerate product engineering, AI capabilities, and go-to-market operations. Key customers across various sectors include Citi, Danske Bank, Chubb Insurance, Puma, Sherwin-Williams, Total Wine, LinkedIn, Wiz, Zscaler, Mistral, Vercel, Ticketmaster, Fanatics, and Axon.
Structure and Roles on Checkly’s Sales Team
The Checkly Sales organization is a lean team of approximately 10 sellers, including Account Executives and Sales Development Representatives. The team is primarily based in the United States, with additional team members in the United Kingdom and Spain.
Checkly divides its Sales coverage into two primary market segments:
- Commercial Segment: Focuses on companies with fewer than 1,000 employees. Account Executives handle high-velocity sales, driving both inbound trial conversions and outbound pipeline generation. The average deal size is around $20,000, and the typical sales cycle length is 45 days.
- Enterprise Segment: Focuses on organizations with more than 1,000 employees. Account Executives partner closely with SDRs on targeted outreach. Deals are typically in the six-figure range, and the sales cycle spans from six to nine months.
Day in the Life on the Checkly Sales Team
Working in Checkly Sales involves managing end-to-end deal execution within a lean startup environment. Daily responsibilities span account research, prospecting, territory planning, customer meetings, and active pipeline management. Because the team operates with minimal overhead, sales representatives frequently take on responsibilities beyond standard job descriptions, offering opportunities for professional growth. Continuous learning is built into the workflow through weekly or bi-weekly training sessions focused on product updates, customer use cases, and industry developments.
The Checkly Sales Interview Process
The hiring process for a Checkly Sales role consists of four structured stages designed to assess personal culture fit, sales methodology, and strategic execution:
- Initial Screening: A 15-to-30-minute introductory phone interview with Human Resources.
- Hiring Manager Interview: A one-hour interview with the Chief Revenue Officer to evaluate background and general alignment.
- Panel Presentation: Candidates prepare and present a standardized prompt covering four key areas:
- Personal Introduction: Details about personal background and interests outside of work.
- Deal Win Analysis: A review of a successfully closed deal, detailing strategy, execution, and success factors.
- Deal Loss Post-Mortem: An honest review of a lost deal to demonstrate self-awareness, coachability, and key learnings.
- Account Prospecting Plan: A strategic outreach proposal for a sample account, including target personas, multi-channel messaging strategies, and follow-up cadences.
- Executive Interview: A final discussion with the Chief Executive Officer and Co-founder focused on cultural alignment, mission fit, and company vision.
Why Join Checkly’s Sales Team
Checkly offers several key advantages for candidates seeking opportunities in modern enterprise tech sales:
- Critical Business Value: Checkly addresses application downtime, which directly protects revenue for enterprise clients across e-commerce, financial services, and travel.
- Market Position: Checkly leads in Monitoring as Code and agentic synthetic monitoring within a rapidly expanding observability market.
- Early-Stage Career Growth: Joining a team of around 50 total employees allows sellers to directly shape company strategy, expand their skill sets, and advance quickly within an international team.
