Hire me, Help Scout!

Welcome, hiring manager for Help Scout!

You are here because I have applied for the currently open Head of Total Rewards 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 Total Rewards at Help Scout

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 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

Some of the responsibilities taken directly from the job posting:

  • You’ll dream up an innovative compensation and benefits administration process, and work with the People team to ensure a thoughtful, comprehensive, and equitable process to reward and retain our valued employees.

    • Employee retention was one of my primary KPIs while at Sandhills Development and compensation was a major part of my strategy for maximizing average employee tenure. With an emphasis on transparency and equity, I built from scratch a data-driven system for determining compensation for all staff. This system proved highly effective at reducing or eliminating pay inequities, incentivizing growth, and improving employee satisfaction. I also administered and designed all of our perks and benefits.
  • You are extremely organized, sweat the small details, and shine when it comes to project management.

    • My work has always been fast paced and I’m well accustomed to balancing a variety of projects simultaneously. For example, while at Sandhills Development, I was the Director of Operations, managing every aspect of the employee experience including compensation, benefits, hiring, culture, D&I, meetings, retreats, and more. In 2021, a change in staffing lead to me assuming the additional role of Product Manager for our eCommerce software product (60k+ users, ~$1M ARR). I took that burden on without hesitation and managed to increase user engagement and develop a brand new product roadmap while continuing to perform my People Ops duties.
  • You’ll support the CPO to develop, prepare materials, and make recommendations for the Compensation Committee and Board of Directors.

    • While serving as the Director of Operations at Sandhills Development, we had a leadership team of about ten people. All members of the leadership team were responsible for authoring detailed plans and drafting pitches for new initiatives. I created more pitches than all other managers combined. For the past five years I’ve worked directly with the company founder to strategize and achieve business goals.
  • You feel at home using Excel or Google sheets and love using data to make sound business decisions and tell compelling stories.

    • ✅ My nickname was “the spreadsheets guy” previously. Data is at the center of everything I do.

Why I want to work at Help Scout

My chief motivation for pursuing a career at Help Scout is an alignment of values. I want to do work that means something and I want to spend my days working with other people who share my inclusive, progressive, global values.

Help Scout fits that description perfectly.

I’ve admired the people and espoused principles of Help Scout for years. As the Director of People Operations at Sandhills Development, I took a lot of inspiration from Help Scout when developing our company handbook, SOPs, compensation system, benefits, and general business practices. Leah Knobler in particular has been a role model whom I’ve looked up to for a long time. The advice she’s shared in the Remote People Operations Slack team has been inspiring and invaluable. Adam Goyette also graciously joined our virtual marketing summit as a guest speaker in 2020.

Many other companies publicly disclose their practices and values, but very few have so consistently reflected a workplace I want to not only be a part of, but also to help further develop.

I could not envision a more perfect next role for me where my skills will be put to better use than running Total Rewards at Help Scout.

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.