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  1. Blog
  2. Partners in Diversity

She Leads: Jaimie Olmstead Is a Senior Agile Process Leader at Alley

Learn more about her experience and how the web development agency makes employee development a top priority

Group of Alley Interactive employees gathering
Photo courtesy of Alley

This article is part of InHerSight's Partners in Diversity series. Discover companies partnering with InHerSight to better support women in the workplace.

Imagine working for a company that values your personal and professional growth as much as you do, offering workshops, seminars, book clubs, online courses, and more to help you achieve your goals. Web development agency Alley is one such employer.

In addition to personal development stipends and conference reimbursement, every Alley team member has a coach who provides guidance and support around the broader arc of that employee’s tenure at the company. That support might include upskilling, tweaking work style, or even talking through work-life balance struggles and knowing when to take some much-deserved personal time, which is another one of Alley's top perks. 

Most highly rated for Ability to Telecommute (they’re full-time remote), The People You Work With, and Flexible Work Hours, Alley encourages employees to work when they like in order to lower stress and make room for life responsibilities. The company also includes mental health days in their paid sick time policy—because full-body health is both physical and a state of mind.

We asked Jaimie Olmstead, a senior agile process leader at Alley, how these people-first benefits have impacted her time at the company. Learn why, according to Olmstead, Alley is an awesome place to work.

Jaimie Olmstead

Senior Agile Process Leader at Alley with five years of experience

Her top three must-haves at work

  • Paid Time Off

  • Ability to Telecommute

  • Sense of Belonging

First off, tell us what you do for Alley. How did you get started and how has your role changed, if at all, since joining the company? 

I first joined Alley back in 2016 as a project manager before our agile transformation. My background was in similar WordPress agency work, but I was new to the world of digital publishing. When I began my work at Alley, we had a strong agile focus (I was sent for scrum master certification within my first month at the company), but we hadn’t yet gone through our true agile transformation where we started working with dedicated teams. I started truly viewing myself as a scrum master around this time, and my title was changed to “agile process leader.” Throughout this time, Alley was providing extensive scrum training, which was incredibly helpful when it came to leading my team and feeling supported by my employer. My promotion to “senior agile process leader” came after a particularly challenging year for my team during which we successfully launched, and I experienced a great deal of professional growth. I’ve also taken on the role as a peer-to-peer coach, which has been incredibly enriching for me.

Alley has substantial programming around employee growth and development. Talk about how that focus has influenced you and your career.

Being able to access my professional development budget throughout my time at Alley has allowed me to attend conferences, increase my library of professional resources, complete training, and obtain certifications. Alley provides a professional development budget of $1,000 for every team member with over a year of service and $2,500 for coaches/directors/principal UX and software developers. In 2020, since attending conferences wasn’t an option, I used my professional development budget to become a certified product owner through Scrum Inc. Most recently, as part of our peer-to-peer coaching program a group of us attended the Leadership for Institute for School Change, which focused on understanding different communication styles and “ways of knowing” so we could further deepen our coaching skills. 

Alley Interactive

Remote company Alley has perfect scores for Ability to Telecommute because...of course they do. But their next highest metric is for The People You Work With, and this comment from one very satisfied rater speaks to that good vibes feel: “Colleagues and leadership are supportive of work-life balance, diversity in the workplace, mental health, and more. Many smart and kind people. The people really make this place the best. Also the remote work is perfect for me.” Click to learn more about how Alley supports and values their employees.

Learn more ›

What about beyond your career? Are there examples of times Alley—the company, your manager, or your team—has prioritized you as a person? 

One of the most valuable things to me as an employee is for my employer to see me for who I am as a person and be able to show up to work as 100 percent my authentic self. This means understanding that 100 percent includes the more challenging aspects of my life unrelated to my work responsibilities (my Bipolar II disorder, ADHD, and PTSD). At Alley, I’ve felt incredibly supported when talking about these challenges, creating a mental health Slack channel for others to talk through these experiences, and also for providing a workplace that allows for me to determine how I work best. For example, the flexible hours and unlimited PTO allow for me to take the time I need to focus on myself and my mental health without guilt and also to work with my team to create a schedule that works for both myself and them. It’s astonishing to me that more workplaces haven’t realized how powerful it can be to put the trust in their employees to know when and how they’ll be the most productive.

Alley’s values are quality, transparency, and accountability. Which of those values has been most present during your time at the company? 

Transparency is probably the most obvious to me. I appreciated that even from day one, during my initial onboarding, I was given a rundown of the company’s current financials and goals. I had never worked anywhere that allowed its employees insight into these sorts of things; not only to view the breakdown of the numbers but to understand what decisions were being made because of these results. I felt like I was being welcomed into the process and discussion of what made Alley Alley and that my input could help shape what Alley would become as well. This continues on with monthly “Town Hall” meetings, where not only are our financials shared but also our eNPS (employee Net Promoter Score) and how this data impacts the decisions the company is making.

What advice would you give women interested in joining Alley?

Alley has been a place where I have been celebrated when I’ve shown up as my authentic self and have always been encouraged to do so. There is a large supportive network of people here who genuinely care about the people they work with. That doesn’t mean just showing they care through the positive, external-facing aspects of the workplace (benefits, transparency, etc) but also being able to sit in the discomfort of mistakes and missteps that have been made along the way. Alley is consistently learning, adapting, and changing based on the input of voices within Alley, which is something that can be truly hard to find.

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