Job Description

Chief of Staff, CTO

United States /

Engineering /


About Attentive:

Attentive is the leader in conversational commerce, reinventing business to consumer communication. Our SMS-first software platform helps everyone from entrepreneurs to enterprises strengthen relationships with their consumers in a new way. Through two-way, real-time, personalized communications, we drive billions in e-commerce revenue and over 5,000 leading brands like CB2, Pura Vida, Urban Outfitters, Jack in the Box, and Coach rely on Attentive to deliver powerful commerce experiences.

The Chief of Staff position combines strategy, operations, project management, and execution skill sets. This role will be responsible for a variety of tasks and projects with the aim of enabling the Chief Technology Officer to be effective as possible.

The Chief of Staff will need to adeptly handle shifting priorities and create order out of chaos. They’ll be responsible for spinning up systems to run day-to-day operations more efficiently. Over time, they’ll be responsible for planning and executing more complex and strategic projects.

What You’ll do @ Attentive

  • Drive operational improvements on day-to-day processes within the Engineering organization
  • Create and ensure the successful execution of new processes to enable the organization to scale effectively
  • Increase the productivity of meetings within the Engineering organization by owning the planning, agenda, notes, and required action items discussed in the meetings
  • Track the successful execution of action items agreed upon during meetings with the Chief Technology officer
  • Conduct research and summarize findings to inform strategic decisions
  • Facilitate consistent communication channels between Go-to-Market functions, product and engineering teams

About You

  • 3+ years of experience managing operations within a high growth technology company
  • You are analytical, collaborative, and outcome-oriented with strong project management and communication skills.
  • You wrangle all the things; You will need to manage many threads at once and effectively hold others accountable
  • You are a driver with high attention to detail with an ability to successfully drive simultaneous initiatives. You rapidly move ideas through execution
  • Exceptional written and verbal communication skills; you have experience drafting internal communications on behalf of leadership
  • You enjoy tackling and solving new problems; you engage across departments to discover insights in the market and within our business & product that shapes decisions
  • Strong interpersonal skills with high emotional intelligence
  • In looking into organizational pain points, you have an innate curiosity to learn about building large complex software systems

You’ll get competitive perks and benefits from health care to home office equipment, to help you bring your best self to work.


Attentive Company Values

  • Default to Action – Speed is our best offense and defense
  • Never Settle – Continuously raise the bar for yourself and your teammates
  • Hard Work Solves Big Problems – Success requires grit and resilience
  • Be Attentive – Work together as a team to drive greatness for our company and our customers

If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience.

At Attentive, we know that our Company’s strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation.