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Head of Engineering



Software Engineering
Waterloo, ON, Canada
Posted on Thursday, October 12, 2023
We believe communication belongs to everyone. We exist to democratize phone service. TextNow is evolving the way the world connects and that's because we're made up of people with curious minds who bring an optimistic, yet critical lens into the work we do. We're the largest provider of free phone service in the nation. And we're just getting started.
Join us in our mission to break down barriers to communication and free the flow of conversation for people everywhere.
TextNow is building the next generation of mobile phone services by disrupting the low end of the telecom market with a breakthrough, free, talk and text service, delivered through an app. It is our mission to democratize phone service that drives us to think big and act boldly. We believe that everyone should be connected, regardless of their income level, and our solutions are innovative and desperately needed by over 100 million consumers in North America. We have ten million monthly active users, over two million daily active users and have crossed over $100M in revenue with high gross margins, multiple quarters of profitability, and cash in the bank. And the opportunity in front of us is much bigger than what we have already achieved.
Position Summary
The engineering organization represents more than a third of the company’s employees with 100+ employees. The engineering team is located throughout the US and Canada. The largest concentration of employees is in Waterloo, Canada, although they represent a minority of engineers.
Our new Head of Engineering will report directly to the COO and be responsible for setting a culture that reflects our company’s unique leadership model. Among other things, we believe strongly in a culture of accountability and respectful candor and want this new leader to partner with us in developing and reinforcing this culture. The organization is early in its maturity stage with the application of vulnerability-based trust, which the company believes is essential to unlock the potential of our talent. The company is also in the process of developing its ability to leverage quarterly goals to align resources to company-wide objectives and hold teammates accountable for measurable results. Continuing to improve the performance of our engineering organization will require someone willing to speak truth, even when it is uncomfortable, and someone with the communications savvy to be respectful while being direct.
We are looking for a candidate with high emotional intelligence, excellent communications skills, commitment to excellence, and a growth mindset to lead our engineering organization to new heights of productivity. This is not just a process driven job to keep the trains running on time. We need someone with a high motor and relentless energy, dedicated to achieving ambitious goals. If you are looking for a place to rest and vest, this is not the job for you.
We also need someone with a range of experiences leading engineering organizations, who has demonstrated the ability to translate strategic roadmaps into tangible deliverables. Most important experiences will be those in entrepreneurial environments and with disruptive technologies that indicate the candidate can act with agility and nimbly adjust to new information. We need someone that can enable team agility and won’t allow process or perfection to prevent progress. The right candidate will balance a relentless focus on execution with a healthy respect for the team and deep understanding of what motivates great performance.
While the focus is on building a high-performance team that adheres to our leadership model, we also seek someone who can assimilate complex information and develop recommendations that guide our company strategy. A solutions mindset and problem-solving skills will enable the right candidate to overcome obstacles to achieve ambitious goals. Bring your perspectives and make us better!

Who You Are

  • Ready to lead through transparent accountability, aligned to strategic priorities and cascaded to all corners of the engineering organization
  • Motivated by mission, and ready to bring a passion for impact and company success that trumps personal or departmental interests
  • Uncomfortable settling for predictable process when agility is the right answer
  • Respectfully candid, wanting to speak truth when it’s uncomfortable, and willing to invest the effort to make sure truth is received in the spirit intended
  • Aware that emotional intelligence is your most valuable asset and understand that listening isn’t just a checkbox requirement, but your most important tool to learn and grow
  • Eager to invest your emotional energy in establishing relationships based upon vulnerability-based trust with your peers in senior leadership and the teams in your organization
  • Know that high performing engineering teams need to know the why to believe in the direction and do their best work
  • A proven leader who has taken organizations through the scaling of business and organization that fits TextNow’s trajectory.
  • Bringing 10+ years of engineering leadership experience at a variety of scales to bear in your decision making. You’re comfortable operating in an environment where you need to motivate teams by working with managers and managers of managers. You’ve grown intimately familiar with hybrid and remote working environments across multiple time zones.
  • Experienced in B2C mobile app engineering and/or communications and telecom technology
  • Located in the Toronto-Waterloo, Ontario Area
More about TextNow...
Our Values:
· People First (Make business decisions by putting people first!)
· No Brilliant Jerks (We're cool with the brilliant part, with the jerk part? not so much)
· Give a Damn! (We care about our work, our mission and our customers)
· Challenge Accepted (Show up with a positive can-do attitude)
Benefits, Culture, & More:
· Strong work life blend
· Flexible work arrangements (wfh, remote, or access to one of our office spaces)
· Employee Stock Options
· Unlimited vacation
· Competitive pay and benefits
· Parental leave
· Benefits for both physical and mental well being (wellness credit and L&D credit)
· We travel a few times a year for various team events, company wide off-sites, and more
Diversity and Inclusion:
At TextNow, our mission is built around inclusion and offering a service for EVERYONE, in an industry that traditionally only caters to the few who have the means to afford it. We believe that diversity of thought and inclusion of others promotes a greater feeling of belonging and higher levels of engagement. We know that if we work together, we can do amazing things, and that our differences are what make our product and company great.
TextNow Candidate Policy
By submitting an application to TextNow, you agree to the collection, use, and disclosure of your personal information in accordance with the TextNow Candidate Policy