Q&A with Shaykara Webster, Chief of Staff at Amenities Health
Meet Shay, the go-to guru in HR and operations, currently shining as the Chief of Staff at Amenities Health. Shay's journey through the HR landscape is marked by significant roles and achievements, from pioneering the HR department at Livepeer as their first HR hire and navigating the company through periods of hypergrowth and challenging reductions in force, to leading people operations for Women Who Code's vast network of volunteers across the globe. Her strategic involvement in people operations and financial oversight extended over 200 technologists worldwide, showcasing her ability to lead and manage at scale.
In addition to her corporate roles, Shay has dedicated her expertise to supporting diversity and inclusion in tech through her positions with Incluzion and The Choose True Project, and co-founding 3MC Business Solutions in 2018. This consulting firm, under Shay's guidance, has provided invaluable support to clients like Microsoft and Wordpress Buffs, leveraging her extensive background in program management, talent acquisition, and diversity/inclusion.
Raised in Columbia, South Carolina, Shay's educational and professional journey is as inspiring as it is impressive, culminating in an MBA with a concentration in HR management from Winthrop University while working full-time in Charlotte, NC. Now residing in Atlanta, GA, with her husband, Shay balances her professional aspirations with a love for travel, movies, and cooking, bringing a well-rounded perspective to everything she does.
Q: What motivated your career transition from global HR roles to Chief of Staff at Amenities Health, and how does your background in people operations enhance your current role?
It wasn't a transition for me. I've always worked in dual capacities between Global HR and Global Business operations, and this role as chief of staff at amenities health was no different because not only do I support the CEO on business operations I also oversee our people operations business function. As we scale and grow I'll eventually need to decide if I want to go the COO or CHRO route and hire someone for the other route, but until then I really appreciate the opportunity to utilize both skillsets. People Operations and Business Operations have so much in common, but having a MBA background has allowed me to leverage both so effortlessly on all of the teams I've supported both fractionally and full time.
Q: Reflecting on your experiences at Livepeer, especially during expansion and reduction phases, what were the key challenges and learnings from scaling teams and leading a reduction in force?
The key challenges are all aligned to learnings, which is something I will always appreciate. Some of the challenges that were recurring for different reasons include timing, financial forecasts, and tough conversations. Timing is a challenge with any growing business, because you won't always nail timing perfectly but there's almost always the 'perfect' time to do everything. From hiring to promotions to organizational structural updates to process improvements and implementations. There's so much to do in a business, and very little time to slow down so you learn how to get things done while moving simultaneously. Financial forecasts is a learning that becomes a challenge when you realize that not everything can be forecasted, especially in a startup. This means that no matter how many financial reports we audited or how far out we forecasted, we could not predict the market occurrences that led to the entire tech industry conducting layoffs, especially web3 technology. Though unfortunate, and not my first time experiencing a layoff - it was my first time leading the behind the scenes of everything that goes into a RIF (reduction in force). The tough conversations you have to have with employees impacted and those remaining is something you never get use to, but with experience and a level of transparency it does get a little easier to digest. The biggest learning of them all, is to remain nimble. Always be willing and capable to pivot. Not just in business, but in life.
Q: Given your commitment to diversity and inclusion through roles at Women Who Code and The Choose True Project, could you share a memorable initiative that significantly impacted diversity in tech?
I'd first like to say that my commitment to diversity isn't a trend like the market adopted some years ago. My commitment to diversity is a part of my personality as a black woman in America. I say this to say, a lot of my learnings and understanding of DEI will come from a lived experience whereas someone who can't relate will get their learnings and understanding from a textbook and it is vastly different. A memorable initiative that significantly impacted diversity in tech was my collaboration with Incluzion. I joined their team as the chief talent acquisition officer, and was able to partner with so many organizations in tech on their DEI initiatives. All of which were measurable and translated to true impact from making candidate experiences more inclusive to increasing diverse candidate reach to hiring more diverse candidates to retaining diversity on the team and developing those hires into leaders throughout the organization. DEI is a full cycle initiative, yet so many organizations only focus on the hiring part of it all.
Q: What drove you to co-found 3MC Business Solutions, and could you highlight a project that showcases your firm’s expertise and your approach to consulting?
Co founding 3MC business solutions honestly fell in my lap. Throughout my career I've taken relationships very seriously, and have been able to build a great rapport with all of my colleagues and bosses. So much so, that many of them would reach out with opportunities after I've moved on to the next stage of my career. Many of these opportunities would be project based or on an as needed basis, and it got to the point where I couldn't support everyone that asked all by myself. Instead of turning them down, I figured it could be a way for me to build a diverse talent pipeline and community of freelancers who have the skill set and expertise for each project request while simultaneously giving minorities access to opportunities that allow them to supplement their income. A project that I would highlight to showcase our firm's expertise is our collaboration with moveon.org. I was able to find their new CTO for them by leading a DEI focused executive search, and I had a team of engineers support me on the technical assessment stage of the hiring process.
Q: How do you balance a demanding career with personal interests, and how has moving across different cities influenced your growth both personally and professionally?
I balance my career with personal interests by leaving work at work, and truly utilizing my calendar & agenda. I typically list out everything I need to complete in a day, with an additional 'nice to knock out' task list. No day is the same, so there are absolutely days where I drop the ball at work but carried it well at home, or vis versa. Acknowledging that every day won't be the same, giving myself grace where needed, and having a supportive husband + family & friends has been my cheat code for balancing work & life. Utilizing my weekends as time away from work and moving across different cities + traveling for fun has allowed me to gain exposure to different perspectives and ways of doing things which is always a value add when you're responsible for creating and implementing new processes, policies, and workflows.
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