Caxy

HQ
Chicago
45 Total Employees
Year Founded: 1999

Caxy Career Growth & Development

Updated on October 13, 2026

Frequently Asked Questions

Career Progression Paths

Growth at Caxy tends to look less like a rigid ladder and more like real opportunity. If you show initiative and do good work, there's room to take on more. Because we're a smaller team, people often get exposure to different parts of the business earlier than they would somewhere bigger, which opens doors that a strict title-based structure usually closes off.

Learning & Upskilling Opportunities

We believe in promoting from within and giving people the room to grow into roles they weren't necessarily hired for. Our COO, Hannah Deason, is a perfect example. She started at Caxy as an executive assistant, learned to code along the way, and grew into leading the company operationally. That's not a fluke story, it's part of how we think about talent here: if someone shows curiosity and puts in the work, we'd rather invest in them than look outside.

Mentorship & Coaching

At Caxy, mentorship is built into how we work. Every employee is a mentor, a mentee, or both, with pairings revisited quarterly as their goals evolve. Whether someone is pursuing our Leadership Track or technical Mastery Track, they receive guidance tailored to their career aspirations.

Our 12-week Performance, Accountability, Commitment (PAC) plan gives employees clear development goals, regular feedback, and measurable milestones. Combined with ongoing check-ins, hands-on coaching, and opportunities to learn from senior leadership, this approach helps employees continuously develop their skills and take the next step in their careers.

Career Progression Paths
Learning & Upskilling Opportunities
Mentorship & Coaching

At Caxy, career growth isn't limited to a single path. We believe in developing talent from within and giving employees opportunities to grow into roles that align with their strengths and ambitions.

Junior and mid-level developers have clear pathways toward becoming architects, technical leaders, and directors. Similarly, project managers can advance into senior product management, account management, and director-level positions.

Our commitment to mentorship and internal development has helped us promote more than 40 employees over the past decade, including five director-level leaders developed entirely from within.

The takeaway: We don't just hire for the role someone can fill today. We invest in who they can become tomorrow.

Caxy's Candidate Tradeoffs

If you’re weighing whether Caxy is the right fit, these are the core tradeoffs to consider.

  • Caxy strongly emphasizes autonomy and ownership, empowering individuals to take initiative and make meaningful decisions, though this can come with less day-to-day guidance.

Caxy Employee Reviews

Caxy is a company where I feel respected and appreciated. I’ve grown not only career-wise but also as a person in my eight years at Caxy.

Employee Image
Tony, Senior Software Developer
Tony, Senior Software Developer

We support growth informally through peer learning, project stretch skills, exposure to new technology, and a broad range of business verticals. We support growth formally through professional development plans, pair learning partners, semi-annual reviews, weekly or monthly check-ins toward goals, and opportunities to take classes / conferences.

Employee Image
Hannah, Chief Operating Officer
Hannah, Chief Operating Officer

What People Are Saying About Caxy

  • Challenging Assignments: Work is described as complex and varied across industries with modern technologies, creating hands-on stretch opportunities. Feedback suggests individuals can influence architecture and solutions, accelerating practical learning.
  • Coaching & Feedback: Development is supported by regular goal check-ins, semiannual reviews, and peer learning mechanisms. Feedback suggests consistent mentor touchpoints and colleague input provide ongoing guidance.
  • Internal Mobility: Movement within the organization is enabled through internal job postings, documented progression frameworks, and an explicit promote-from-within stance. Examples of employees stepping into broader responsibilities indicate visible advancement paths.

Caxy's Benefits

Allows employees to pursue continuing education during work hours

Defines roles and sets expectations for success

Encourages knowledge sharing and cross-functional collaboration

Hosts Lunch and Learns

We have dev talks where developers will pick a topic to research and present. Open to anyone who has a topic they are excited about.

Job training & conferences

We have numerous personal one on one training and subscriptions to training sites that employees are encouraged to use.

Managers hold regular development check-ins

Offers apprenticeship programs

Offers mentorship program

Everyone here has a charted career path. We have senior people attached to growing team members to help them level up.

Provides continuing education stipend

Where appropriate, we provide this.

Provides formal manager training and leadership development

Provides online course subscriptions

Most developers have access to frontendmasters and AWS. As needed, most junior team members have access to Lynda or coursera. All leads have a masterclass as of 2026.

Provides opportunities to take on expanding responsibilities

Provides paid industry certifications

As appropriate or needed for their development and the business we pay for this. It's included AWS, big commerce, and Content Stack certs as well as PMPO / CSM / CSPO / PMP certifications.

Provides personal development training

Provides structured early-career growth opportunities

Provides structured onboarding for new employees

Provides training support and resources for AI adoption

We have curriculum for AI adoption, we have an ethical and practical use for AI, and we have hackathons and ideations sessions for further AI. Dev meetings are often centered on this.

Supports employee-driven initiatives, not just top-down priorities

Documented career progression frameworks

We use PAC plans and development tracks in mastery and leadership to make it clear how you progress. Our roles are numbered for progressions as well.

Documented internal promotion policy

We require that all roles (except sales) are made available for internal employees to apply. These are communicated in all-hands or through management feedback.

Documented path to leadership development

Posts new positions internally and encourages employees to apply

Prioritizes promotion advancement based on impact

Prioritizes promotion advancement based on long-term contribution

Promote from within

Wherever possible and practical for the business, we promote from within. 90+% of our leadership positions are held by folks that were promoted from within.

Provides customized development tracks

We have custom PAC plans (performance, accountability, commitment) mentorship programs for all team members that want them. Our technical team members sign up for mastery or leadership tracks.

Regularly scheduled promotion review cycles for employees

We assess roles at least every 12 months.