Careers at Cirrus Insight

Chief Technology Officer

Cirrus Insight is looking for an experienced Chief Technology Officer to contribute to Cirrus Insight’s strategic and financial outcomes by defining and leading the company’s overall technology landscape, and building and leading a sensational team. Scaling operations, developing management talent, and defining and installing robust processes and standards are just a few of the challenges that will need to be accomplished to advance the fast-paced, growing organization.

As a key member of the executive leadership team, the CTO will have direct impact and play a critical role in the company’s long-term growth and success.

This role is responsible for ownership of all technology, technology services, product delivery, support, and defining Cirrus Insight’s global technology roadmap and vision. Reporting to this CTO will be all software development, quality assurance, technical operations teams, support, and IT, comprising 40+ full time employees and several specialist contractors.

Location: United States

  • We have a geographically distributed team. Most of the engineering team is in Irvine,
    CA along with remote and offshore teams.

Primary Responsibilities

  • Make our customers successful by providing a fast, stable, reliable, and trustworthy system that helps them do their jobs better every day.
  • Make our team successful by hiring, retaining, and growing experts and leaders at every level who can set expectations clearly and deliver on their commitments.
  • Make our company successful by delivering a team and platform that can scale profitably to support rapid growth, enterprise scale, and market-leading innovation.


  • The engineering team will be at the center of the strategy that transforms the company. The CTO must set goals and build alignment around clear, achievable milestones for delivering on that strategy.
  • Establish business, resourcing and talent plans for delivering high-quality product on time per the product roadmap and agreed upon timelines. Be a leader around hiring standards to drive the attraction and retention of superior talent.
  • Articulate long-term and short-term strategy, factoring in realistic execution and change management goals.
  • Lead and manage a geographically distributed team. Most of the engineering team is in Irvine, CA, support in Knoxville, TN as well as offshore teams; establish and champion processes to enable smooth collaboration across offices and time zones.
  • Identify critical decision points and drive towards strategic clarity on near-term and medium-term roadmaps, with a consideration of trade-offs, cost, product roadmap, customer needs, and strategic implications.
  • Oversee numerous projects in parallel, prioritizing resources effectively, and being pragmatic about what can be done given resource constraints.
  • Partner with the CEO to align on short-, medium- and long-term product and feature roadmap.
  • Develop a comprehensive technology agenda for cloud operations to enable the business to grow and scale in a profitable way as a best-in-class enterprise SaaS vendor.
  • Lead agile planning and development practices to maximize the efficiency of software delivery.
  • Ensure continuous availability of the Cirrus Insight platform.
  • Define and implement the optimal organizational and functional design to facilitate DevOps capabilities and behaviors.

Primary Requirements

  • Demonstrated ability to build and retain world class Engineering, QA, and DevOps teams
  • Excellence in architecting, delivering, and supporting a highly available SaaS platform in AWS
  • Ability to prioritize asks, set expectations to stakeholders, and deliver releases on time


  • 15+ years of progressive leadership experience in a software engineering or technology organizations while operating as a senior executive, with demonstrated technical and business acumen.
  • Currently, or have been in the recent past, responsible for engineering and operations of commercial, enterprise SaaS products.
  • Ability to architect and deliver a highly available, enterprise-grade SaaS solution using the AWS cloud.
  • Experience with a variety of Salesforce integrations, including synchronous and asynchronous approaches.
  • Experience developing and deploying browser extensions direct to consumer and throughout an enterprise landscape.
  • Experience building, managing, and supporting extensions to modern versions of Microsoft Outlook
  • Experience developing, deploying, and supporting extensions and add-ons to webmail platforms, including Gmail, G Suite, and Office 365
  • Ability to implement an end-to-end CI/CD pipeline designed to speed up iterations and enable more frequent releases.
  • Expertise in Quality Engineering, including the measurement and reporting of release quality metrics.
  • Ability to define a comprehensive, proactive metrics, analytics and monitoring strategy to serve enterprise customer needs.
  • Thought leader in a disciplined delivery methodology e.g. Agile, Scrum
  • Experience implementing DevOps tools and processes from the ground up
  • Exposure to a formal product management discipline, e.g. Pragmatic Marketing framework
  • Proven ability to translate strategy into sound operational plans and roadmaps, delivering new products to market. Prior experience in fast-paced or start-up, agile environments
  • Established ability to examine and re-engineer operations and procedures, formulating policy, and developing and proposing new strategies and procedures.
  • Prior experiencing setting and executing on a SaaS strategy including cloud architecture, building the correct team/skills, understanding of cost optimization, shortening the onboarding time and provisioning.
  • Customer facing - excellent written and verbal communication skills; proven experience articulating security and risk-related concepts to all audiences, including C-level executives, customers and board members.
  • Demonstrated experience hiring, managing, developing, and retaining highly technical staff.
  • Demonstrated experience partnering with executive-level stakeholders to drive change across multiple business functions.
  • Outstanding interpersonal skills; proven ability to work effectively with technical contributors, management and executive leadership.


  • Be a knowledge leader - and champion for Cirrus Insight customers.
  • Operate with a strong work ethic - an unrelenting resolve to follow through and meet commitments.
  • Thrive on challenges - act with appropriate urgency, and celebrate wins!
  • Be purposed - focused on the right outcomes through inclusive ideation leaving egos, politics and hierarchy aside.
  • Innovate - ideate and deliver new ideas, processes and ways of delighting our customers.
  • Communicate transparently - listen actively, and speak respectfully.
  • Lead - a team full of folks who are proud to work in tech improving the work process and output of their customers.

Hiring Process

This is a retained search. If there is mutual interest on both the part of the candidate and Calibre One, the next step would be a face to face interview (where possible), as a precursor to being introduced to Cirrus Insight.

Contact Details

Diane McIntyre
Managing Partner

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