As one of five apprentices in WePay’s pilot apprenticeship program, I have been working for the last six months as an entry-level software engineer. As a nontraditional junior developer with a bootcamp background, I want to share what WePay’s apprenticeship program is, what I do as an apprentice, and why learning from WePay’s strong engineering culture has set me up for success as a software engineer.

WePay’s Apprenticeship

In developing a software engineering apprenticeship, WePay has joined a growing number of companies diversifying their workforces and building stronger pipelines for entry-level talent. Apprenticeships are essentially extended internships, focusing on team integration versus completing a project for the duration of the program; the goal is to convert apprentices into full-time entry-level engineers by getting them to the same skill level expected of an entry-level SWE. At WePay, the greatest indicator of success for SWEs isn’t knowing everything about everything, but rather that an intellectual curiosity and willingness to learn–supported by a record of learning–is more important than flawless technical skills. In developing WePay’s program, Matthew Clower (Chief Software Architect) specifically targeted candidates without degrees in computer science. While this is a seemingly odd requirement for a software engineering program, careful consideration and discussion led to an apprenticeship that he notes “taps into the incredible cognitive diversity coding bootcamps offer, selecting apprentices who are curious and eager to learn. Because bootcamp graduates often have trouble landing jobs as software engineers, WePay provides the apprenticeship as a launchpad for software engineers without a computer science background to start their careers.”

WePay’s apprenticeship is a six-month, full-time commitment. Apprentices are placed on one engineering team and rotated to a new team halfway through the program. In terms of day-to-day work, there is little difference between an entry-level SWE and apprentice; the major differences are performance expectations and apprentice resources. In addition to the contextual knowledge an apprentice’s team and manager would have regarding their background and expected skill level, apprentices are provided with:

  • A mentor/coach: a staff-level or above engineer for the duration of the program

  • Weekly curriculum to help to fill in computer science knowledge gaps

  • Scheduled 1:1s and group facetime with C-Suite level leaders

  • Regular feedback from program leaders

The beauty of apprenticeships is the agreed-upon noncommitment from both parties; if an organization has invested in a candidate who is a poor fit or a candidate decides to seek employment elsewhere, each party has a defined timeline and exit.

Why an apprenticeship?

Like most bootcamp graduates, I did not have a tech background. I worked in higher education, editing, and public relations before deciding to pivot into software engineering. I graduated from Hackbright Academy and immediately applied to a mix of regular entry-level positions as well as apprenticeships. My goal was to work for whatever organization gave me access to the best engineers/practices and exposure to as many sides of engineering as possible. Because I was honest with myself about my technical skills and knowledge base (let’s just say I wasn’t surprised to learn that I was NOT a secret programming prodigy), I leaned more towards apprenticeships due to the additional resources and lower bar for entry. I quickly learned through my job application experience that how a company interviews candidates speaks volumes about their engineering culture. Despite receiving offers for entry-level SWE roles, WePay’s interview process and initial offer gave me enough confidence in what I would be gaining that I had no hesitation in accepting an apprentice position.

What is working at WePay like?

Before switching careers, I had enough real-world work experience to recognize WePay’s unique culture. Due to the pandemic, I received all of my fancy equipment at home, shrieked in excitement over the WePay swag, and signed in to the IT setup call. I was blown away by the care and attention taken to ensure that I wasn’t lost, and that feeling of being completely supported hasn’t ever gone away. I was sure the honeymoon would end after a few weeks, but from my first IT meeting to lunch calls to coffee chats with executive leadership to daily scrum with teammates–each and every interaction was so genuine that I knew I had found something special.

WePay has a well-documented set of company values, but what stands out most are its communication, pedagogy, commitment to diversity, and broad spectrum of resources. With the newfound normal of working at home and interacting via Slack and Zoom, WePay has done an excellent job of persisting a highly communicative culture. There are no barriers to access, and even with a vertical organizational structure, communications are horizontal. I feel as comfortable slacking a VP as I am another apprentice. Speaking up in meetings with C-level executives has been as easy as jumping on an ad hoc Zoom call to discuss a ticket with a teammate.

This is largely due to the way engineers communicate and an emphasis on transparency. WePay is really good at hiring people who can explain things well, at all levels. By hiring engineers who are kind, smart, and communicative, the onboarding ramp is much easier to climb than it might be elsewhere. Everyone is willing to not only answer questions, but also to teach principles and processes that improve my daily work experience. And by everyone, I mean everyone, at all levels, in every department. Between executive leadership, team managers, teammates, sales team, finance, administration, HR, and everyone in between, every person I’ve talked to has answered my questions and explained difficult concepts, technologies, policies, services, and software at high and low levels.

I’ve also been pleasantly surprised by the high utility of communication skills in engineering. Between daily meetings, intra- and inter-team collaboration, one-on-ones, skip levels, book clubs, team-building, Slack channels regarding personal interests (e.g. game night, pets, music, etc.), there is no shortage of work and personal opportunities to connect with others. This, in addition to a culturally valued emphasis on diversity and inclusion (demonstrated explicitly in company policies and activities, as well as implicitly in interactions with colleagues) has not only supported my desire to perform well by seeking out sentient resources at WePay over non-sentient web resources when I come across a problem, but also given me access to a community in which I truly feel welcome.

What do I actually do?

There is a scary amount of trust and flexibility as an SWE. While there are structures in place to organize seniority and work, there’s no one to watch over your shoulder and keep you on track. Rather, the culture reinforces trust in each other to complete assignments, speak up when you need help, and communicate progress honestly.

Though the format and dynamic differs between teams, there is a daily scrum to touch base with your team. This is a brief discussion of what you did the day before and what you plan to work on for the day. As an apprentice, I meet daily with my “buddy” (a teammate assigned to mentor me, answer questions, and help with onboarding). Other than scheduled meetings, the day is mine to work on my tickets and reach out for help when needed. If I hit a problem, I typically reach out first to my buddy (if I don’t already have a specific contact with contextual info), then to my team, then I follow wherever that thread takes me until my problem is resolved. I have three young children, and have found that the flexibility in working has been critical to being productive. I appreciate that I can set my work hours outside of necessary meetings, and that my colleagues are gracious about interruptions, understanding of last-minute changes, and respectful of family time. In between work, there are also regular events which have included cooking classes, workout classes, painting events, game nights, scavenger hunts, and other unofficial online gatherings.

What works well?

Even though I haven’t yet felt comfortable or confident that I’m exceeding expectations, I have never felt like I’m drowning. It’s more like frantically treading water with the wall in sight, I know no one will let me drown, and there are people cheering me on and reaching out a hand when I need it. Because WePay’s culture reinforces collaboration and communication, I’m not scared to ask for help. By having honest discussions about what is expected of me as an apprentice, the pressure to know everything and do everything perfectly is immensely alleviated. In fact, I have been actively encouraged to let go of the wall and make mistakes so that I can walk through them, learn from them, and re-orient myself to new information.

My favorite part of choosing to pivot into software development? There is a camaraderie built on the shared experience of adjacent problem-solving. Every engineer understands the euphoria of struggling through a problem, then finally, finally! getting that successful build. The endorphin rush of solving the breadcrumb trail of software engineering tasks means that I’ve yelled out loud in triumph, fist-pumping the air more in the last six months than I have in my entire previous working life–and every engineer at WePay can relate. Even though I’ve worked long hours and dreamed in code and have had little mental capacity for anything outside of work, I haven’t had a single day that I’ve dreaded logging in and tackling my sprint tickets.

In addition to the many ways I’ve felt supported in my career transition, the best part of choosing an apprenticeship with WePay has been the rapport with other apprentices. Because of our nontraditional backgrounds and the experience of joining WePay as a cohort, we have found support, assistance, and learning in each other; while this has been mostly self-initiated, WePay provided the forums and opportunities to learn with and help each other. We have regular apprentice standups, demos, a personal thread for questions and achievements, and often use each other as the first line of outreach. At the halfway point of the program when we rotated onto new teams, it was incredibly reassuring to have a resource with the exact experience and information I needed.

What are the main challenges?

There is incredible frustration in having to ask questions about everything, all the time. When you’re used to getting things done and finding answers independently, it is uncomfortable to just get over yourself and ask your “dumb” question. There’s also a special kind of anxiety in working through Zoom as a teammate tries to help by directing what to click on or type, while not having a full dictionary of tech jargon at my disposal. Imposter syndrome is a recognized, openly discussed part of the work environment; luckily, in a supportive engineering culture like WePay’s, engineers are patient, kind, and great at reiterating that it’s normal not to know everything. Learning to context-switch effectively is also challenging, as well as managing time in large enough chunks to be productive, but small enough chunks to progress. Lastly, getting feedback can be hard before you realize that assessments aren’t personal. What might be perceived as critical feedback is really just an assessment of what needs improvement. A highly communicative work culture means problems are identified so they can be fixed, and honesty results in improvement. No one gets credit for pointing out a problem without doing anything about it, and this has taught me to ask for specific feedback and receive it with a growth mindset. I believe that everyone at WePay wants me to succeed, and this process of learning and growing, though difficult, has taught me valuable lessons.

Would you still choose an apprenticeship?

While there are disadvantages to choosing an apprenticeship program over a regular, full-time role, the pros have outweighed the cons in my case. Because I have confidence in WePay’s commitment to invest in my training and success, I have gained invaluable, real-world experience that will be an asset in the next steps in my career. While technical and practical skills are the obvious prize of the program, I feel fortunate to have seen how an engineering environment contributes to individual growth. While some might have weighed joining WePay’s initial apprentice cohort as risky, my calculated risk–as well as WePay’s–was fruitful. Of five apprentices, all were offered full-time SWE positions, with 100% acceptance. I am excited to continue at WePay as an entry-level SWE, maintaining the momentum of my software engineering education while on the job and positively reinforcing my decision to enter this field. Transitioning to a career in software engineering has many growing pains, but these can be turned into strengths in a supportive, pedagogical, communicative engineering culture, which I’m happy to say is thriving at WePay.

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