Hire me, Upstatement!

Welcome, hiring manager for Upstatement!

You are here because I have applied for the currently open Director of People position. I appreciate you taking the time to consider me for this role. I’m confident you’ll be glad you did.

Please allow me to introduce myself…

Why I’m a perfect candidate to lead People at Upstatement

People are my passion

I was born to lead teams and thrive when given full responsibility for all things People Operations. My personal mission in life is to uplift others and that’s what I’ve continued to do in my people leadership roles. While serving as the Director of Operations for multiple software companies, I’ve been instrumental in hiring best-fit talent, developing vibrant teams, creating talent strategies which serve business goals, championing Diversity & Inclusion, and raising the standard for employee experiences.

At Upstatement, I will bring an insatiable appetite for continuously improving the lives of our people in ways which improve retention, aid recruitment, and drive growth.

I’ve built complete compensation systems from the ground up

At Sandhills Development I created a sophisticated, bespoke, and transparent system for determining employee compensation which turned a company weakness (low employee pay satisfaction) into a strength (over 90% satisfied with pay after implementation). I incorporated compensation data from sources like PayScale, Culpepper, Glassdoor, and others to ensure our pay was fair and equitable.

This compensation system also included a detailed, easy to use, and effective career progression framework (a topic I love talking about) which provided our entire team with crystal clear incentives to improve and grow.

I have designed, implemented, and managed all kinds of benefits and perks

Health insurance, 401k plans, equipment purchasing, PTO, company holidays, profit shares, parental leave, and all other common offerings have been completely managed by me for the past 3+ years. In addition, I’ve been able to take inspiration from our expressed values (and a little creativity) to implement meaningful perks and benefits such as an annual vacation stipend, Arbor Day tree planting, an “Unplugged bonus”, and more.

In every case, I’ve consulted with ownership to discern our strategy and goals which I then translate into action. For example, ehen employee engagement became a priority, I created a popular “Sipscription” benefit and coordinated virtual gatherings. To that same end, I planned and organized numerous events like these: 2017,  2019, and 2020 virtual. When employee retention became a KPI, I worked to address low satisfaction with pay by creating a data-driven, transparent compensation system which dramatically improved how our staff felt about pay. I also created a career progression framework which gave every employee a clear path forward so that no one felt that leaving the company was necessary in order to advance their careers.

Deep management experience

For the past twelve years, I’ve been managing employees across all disciplines. I’ve had developers, designers, marketers, tech support agents, business development managers, engineering managers, support managers, and product managers, report to me at various stages and have consistently been able to establish close, productive working relationships with all of them. I make it my personal mission to help each of my direct reports accomplish their career goals. I have a very strong track record of guiding, mentoring, and ultimately advancing more junior employees whom I’ve worked with.

I satisfy every requirement for the job

Requirements taken directly from the job posting:

  • 5+ years leadership experience in HR, Talent, or People roles

    • I’ve spent the past five years fully owning all things People Operations at two different software companies. Every process from employee onboarding to equipment purchasing was mine to design and manage. Every aspect of employment with these companies, from compensation to performance evaluations to travel bookings was under my purview.
  • Confident leadership and communication style when presenting to leadership, direct reports, and company-wide

    • I am extremely comfortable and capable when it comes to communicating and presenting to diverse groups. I’m a very experienced and practiced public speaker, having presented at 40+ conferences and been a member of Toastmasters for over five years. For the past four years, I have been responsible for facilitating all company-wide and departmental meetings.
  • Deep understanding of pay strategies, market trends, and compensation benchmarking

    • I developed our entire compensation strategy from scratch using data sources such as PayScale, Culpepper, Glassdoor, and others. I have developed strong opinions and demonstrated repeatedly successful strategies for optimizing compensation.
  • An empathetic problem-solver who can see all sides of any given situation

  • Working knowledge of visa and immigration policies

    • ✅ While serving as Operations Director for a global team, it was entirely my responsibility to understand everything effecting my colleagues’ ability to travel. I routinely had to write letters of recommendation for our visa applicants and help guide them through the process.
  • Experience in a tech or agency setting a plus

    • ✅ All of my experience over the past ten years has been in the tech industry, roughly half spent running an agency and half helping manage software companies.

Why I want to work at Upstatement

I want to do work that means something and I want to spend my days working with other people who share my values for inclusivity, diversity, and technology. Upstatement fits that description perfectly.

Upstatement’s seven core beliefs paint a clear, inviting, and inspiring picture. I’m particularly enthusiastic about working on a team which prioritizes “making each other better”. Lifting up others is at the heart of everything I do.

I’m not looking for a cushy job. I want hard problems and meaningful work. That’s what Upstatement offers (comments like these suggest this is the case) and its why I’m prepared to do whatever it takes to join the team.

Note: I observed an error in the second paragraph on the Upstatement values page: “While it’s easy to see the work do, it’s harder to see how we do it” – > there’s a missing “we” before the first “do”.

What others have to say about working with me

Don’t just take my word for it. Here are former colleagues voluntarily endorsing me:

Steve Bennett, Co-founder, Real Big Marketing (former business partner)

“…You can’t ask for a more well rounded individual.”


Pippin Williamson, Founder and Managing Director, Sandhills Development (former boss)

“Kyle is one of the most dedicated, hard-working, and caring people I have ever had the opportunity to work with”



Tyler Lau, Partnerships Manager, Sandhills Development (former direct report)

“…we were very lucky to have {Kyle} on our team.”


Adam Silver, founder, ConciergeWP (former client and podcast co-host)


Kyle constantly amazed me with his industry insight and original approaches to solving problems. He consistently demonstrated a strong work ethic and has a dedication to success.

Kyle brings intelligence, creativity and leadership to any project he is involved in. On account of his mature approach to his responsibilities, I often thought of Kyle as a colleague I could always rely upon to get the job done. I have always felt he was one of the best in class and it was a pleasure working with him.


Mandy Jones, Content Manager, Sandhills Development and Paid Memberships Pro (former colleague)

2020-02-11 10.18.55

Without a doubt, Kyle is one of the most valuable, hardworking, genuine, and thoughtful people I have ever met. After working with him for over two years at two different companies – Sandhills Development and Paid Memberships Pro – I know his character very well, and feel particularly well-suited to vouch for him as a friend and colleague.

Since I’ve known Kyle, he has brought tremendous value to the teams we’ve been a part of together. He not only pioneered a game-changing career progression framework and made massive efforts in planning and organizing events as Director of Operations at Sandhills Development; He also spent countless hours getting to know his colleagues (including myself) on a personal level.

It’s always been obvious that Kyle is totally invested in helping everyone on his team reach their highest levels of performance and personal satisfaction. Plus, his ability to see different perspectives and potential outcomes make him an excellent communicator and strategist across multiple arenas.

However, even with his creative talent, mind for business, and technological savvy, what strikes me most about Kyle is his kind, earnest nature. He is truly the kind of person you want on your team – the full package.


Ross Johnson, General Manager, 3.7 Designs and Snap Orbital (former co-organizer)

He is wise well beyond most people I’ve encountered in my life. He is incredibly loyal and trustworthy…and an excellent leader.


You can read more positive comments about me in the Recommendations section on my LinkedIn profile.