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I first joined Chili Piper when we were 70 employees, the first People Ops hire at the company.
There wasn’t a recruiter, there wasn’t HR — none of that existed.
So when our Co-Founders, Nicolas and Alina, tasked me with doubling the company, I had a wild idea.
Instead of just building out a recruiting team, I wanted to build an entire system designed to bring talent in the door and make sure they actually wanted to stay. To help them grow and develop.
So during the interview process, I asked them, “Do you have a ‘People’ person? Do you have this kind of system in place?”
Initially, a People person was part of their phase two plan, and we were still in phase one.
But I knew it couldn’t be later. It had to be now — otherwise, we’d be filling a leaky boat. I wanted to bring this vision to life, so I asked if I could do it at Chili Piper.
Luckily for all of us, they agreed.
When we were building the People department, I kept coming back to one thing — making sure we were taking advantage of the talent we already had on board.
I knew we were opening up a lot of new roles, and selfishly, I didn’t want to have to start from scratch. Going out into the wild and finding people. I knew that this talent was probably already at Chili Piper, likely sitting in an SDR seat or some other position, waiting to be utilized for varieties of potential.
I started thinking: how can we “get lazy” with our recruiting and fill these critical roles with talent that already knows the organization, that already knows the problem — that already works here?
And so, the Piper Plan was born.
The Piper Plan is a document, unique to every person in the organization, that allows them to outline their ideal career path — and nothing is off limits. It quite literally asks the question: “What do you want to do?”
Based on these documents, we know whether or not the talent we need for new roles already exists in the organization.
Since then, it’s taken on a life of its own and grown into an entire Talent Development department. More on that later.
Our team motto is: We engage, hire, and develop the best talent in the world.
Above all, we’re about humanity first, with everything else built around it. At every step of our employees’ journey — engaging them, hiring them, developing them — we want to make sure we’re focused on them as people.
Which leads us to why we have to structure our team in a specific way.
Here’s a look at the current structure:
Talent is our core recruiting department. The reason our talent team is special is that they’re recruiters backed by an Ops department.
Why is this unique? Because it usually only happens at companies that are 1000+ people. But we knew we wanted to invest in Recruiting Operations and People Analytics in a more meaningful way.
So we did it at 100 employees.
En-Szu, our Manager of Talent Operations, has built a robust recruiting tech stack to make our team mega-operational and data driven.
Here’s our current recruiting tech stack:
This means that our talent team doesn’t need recruiting coordinators — we just have really amazing recruiters who are backed by systems that do the admin work for them.
This allows our recruiters to double-down on our human-first approach to talent acquisition: building relationships and providing excellent candidate experiences at scale.
In addition to Talent, En-Szu also built out our People Analytics and Operations. This department covers everything from headcount planning to compensation philosophy to People processes.
The fact that our people department functions as data-driven as most sales and marketing departments is by design. ‘People’ should get the same strategic support as other teams.
So why doesn’t every company do this?
Unfortunately, a lot of companies think the way to solve problems is to throw bodies at them (ie. make hires for everything). We see it so many times, and it never ends well.
Companies that scale irresponsibly wind up in situations where they have too many people, or they haven’t had the growth they’ve anticipated, and end up cutting a large number of their workforce to make up for it. Layoffs occur.
That’s the wrong way to grow an organization.
The smart way is to hire someone strategic who can put systems and processes in place that make the need for admin work completely obsolete.
Then, instead of spending a ton of money on an administrative role, you spend a tenth of that on a tool and take that cost savings and apply it toward a senior hire that can actually move the needle for your organization long-term.
Another reason why Ops is important?
Companies say that they’re passionate about DE&I (diversity, equity, and inclusion), but if they don’t have a strong people analytics function, then everything they’re saying is lip service.
Because if you can’t measure it, then you don’t know what you’re driving. You don’t know if you’re actually moving the needle for URGs (under-represented groups).
Hear En-Szu talk more about it here.
As I said, we believe in humanity first at Chili Piper. In fact, we have an entire department dedicated to the experience of being a human being here (aka. a Piper).
Hallie, our Senior Manager of Employee Experience, has built a department responsible for creating a seamless experience from the day Pipers sign their offers to the day they leave our organization to reach new heights.
We accomplish this (surprise, surprise) with lots of tools and systems.
Pipers get robust onboarding communication flows (thanks Greenhouse), welcome packages when they start work (thanks Sendoso), personalized & ongoing training (thanks WorkRamp), and they can even tell us exactly how they feel about all of it in regular engagement surveys (thanks CultureAmp).
Our commitment to growth for our Pipers runs deep. Our co-CEO Nicolas sums it up well below:
“At Chili Piper, our SDRs have the choice to go and work in any department afterward. We strongly encourage our SDRs to change. We have SDRs who’ve become product managers. SDRs who’ve become customer success reps. SDRs who’ve become event managers. We have no restriction on the possible path.”
So how do we make sure that our team, SDRs included, get on the right path for them?
Enter Nalani, Director of Talent Development and Coaching.
Nalani built a team of accredited Talent Development coaches who partner with Pipers, own Piper Plan conversations, and drive outcomes that benefit Pipers and, by extension, our organization.
This needs its own section to talk about.
When companies think about their People function, there are a lot of different schools of thought.
There’s the old school, “HR” mindset which is: Humans are a resource that you can manage just like any other resource in the company — financial or otherwise.
Fundamentally that’s not how we view things at Chili Piper.
When building our people department, we’ve taken great care to make sure we’re empowering the human beings that work here as opposed to empowering the company.
If you genuinely empower people, and it’s your primary agenda as a People department, then the company will profit — there’s no way it can’t.
Not only does it help us from an attrition standpoint, because we genuinely invest in employees and they want to stay, it means that our teams benefit from humans doing the best work of their lives.
This brings us to the difference between learning and development.
Historically, People functions treat L&D as one thing. One department. But at Chili Piper we believe that human beings are on a development journey, and performance is not about people.
Learning (synonymous with training) is specific to the role in which people sit, whether it’s a marketing role or an SDR role — and that falls under Employee Experience.
Development is how people can grow as human beings — and that lives under the Talent Development department.
The reason why that distinction is important is that when employees are underperforming in their role at companies that treat humans like resources, it becomes about the person not being good enough.
We don’t view it that way.
We view it as: The person is good enough (every human is), they simply might not be in the right role for their skillset which is why their performance might be lacking.
That’s why I put so much emphasis on aligning the person to the right role, and why there’s a whole department around development.
So why exactly do learning and development have to be separate?
Because performance conversations can be very sensitive. And when that sensitivity is anywhere near development conversations, which are inherently vulnerable, it can be problematic.
For example, we have Talent Development Coaches at Chili Piper: the full-time, accredited coaches I mentioned earlier whose sole purpose is to partner with employees on their developmental journey.
If there was ever a space where an employee was having a “performance issue” like not hitting their quota, and they take it to their development coach for help — this person who knows their deepest darkest secrets and aspirations — if that coach has any hand in the employee's performance review, it fundamentally alters the relationship.
It means that you can’t have that trust that’s critical for your own development. Which is why we take great care to separate the two.
Getting to this point didn’t come without challenges and mistakes.
If I were to give myself advice, there are some things I would do better. Unfortunately, I can’t go back in time, so I’ll settle for imparting my wisdom on you.
Progression App is our career development tool. It’s an awesome tool, but the tricky part is building out the skill frameworks for every single role.
The progression maps, which detail how to get from point A to point B in your career, took a very long time to create.
How could I have done that better?
First, I would’ve done a better job of getting buy-in — company wide — on why it was important before embarking on this journey.
I was fortunate enough to have Nicolas and Alina on board from the jump, but it was a matter of convincing other departments along the way. Asking managers to build out their team’s progression framework turned into an ordeal and took a lot of reminding.
If I could go back, I would’ve approached it as, “look at the amazing ways you can take advantage of the talent you’ve already hired! And you don’t have to sift through resumes or sit through interviews all day long.”
But I didn’t do that. 😅
And while now everyone is very thankful for it, at the beginning… it was a lot.
Initially, when I thought about talent development I just thought we needed someone to manage the Piper Plan initiative.
Now that we have Nalani, our Director of Talent Development and Coaching, on board, it’s become clear that there’s soooo much more to talent development than just Piper Plans.
It’s an entire coaching, leadership development, and strategic partnership department — and I would’ve started that sooner.
Maybe not the most surprising thing, but the most serendipitous thing that’s allowed a lot of this is that Nicolas and Alina are very much tool people. They’re software people. In fact, Nicolas doesn’t believe in hiring any administrative roles at Chili Piper.
Initially, that horrified me.
But I quickly realized he had a point. And part of the reason this structure even exists to begin with is him telling me, “You’re not going to hire a recruiting coordinator.”
So I needed to figure out an alternative.
The best way to do that was to invest in Recruiting Ops. I had seen how efficient it made other companies, and I didn’t have a choice but to be efficient. Luckily, it all worked out and ended up being really amazing.
The other thing I’ve learned?
It’s really possible to build a people-centric department that still relies on systems and data — two things that don’t seem inherently people-centric.
The fact that you can use software and numbers and math (see, kids? You can use math in real life!) to actually benefit human beings is pretty amazing.
Historically, HR departments have been known for scary things like, “We have to save money — let’s cut benefits here and do this there.”
But when you use the same math to show why it’s valuable to invest in employees, that’s the good stuff.
If you want to build out a human-first team, you’ll likely need some tools to get started.
If I had to rank our tools for how much we love them, it would be:
I first joined Chili Piper when we were 70 employees, the first People Ops hire at the company.
There wasn’t a recruiter, there wasn’t HR — none of that existed.
So when our Co-Founders, Nicolas and Alina, tasked me with doubling the company, I had a wild idea.
Instead of just building out a recruiting team, I wanted to build an entire system designed to bring talent in the door and make sure they actually wanted to stay. To help them grow and develop.
So during the interview process, I asked them, “Do you have a ‘People’ person? Do you have this kind of system in place?”
Initially, a People person was part of their phase two plan, and we were still in phase one.
But I knew it couldn’t be later. It had to be now — otherwise, we’d be filling a leaky boat. I wanted to bring this vision to life, so I asked if I could do it at Chili Piper.
Luckily for all of us, they agreed.
When we were building the People department, I kept coming back to one thing — making sure we were taking advantage of the talent we already had on board.
I knew we were opening up a lot of new roles, and selfishly, I didn’t want to have to start from scratch. Going out into the wild and finding people. I knew that this talent was probably already at Chili Piper, likely sitting in an SDR seat or some other position, waiting to be utilized for varieties of potential.
I started thinking: how can we “get lazy” with our recruiting and fill these critical roles with talent that already knows the organization, that already knows the problem — that already works here?
And so, the Piper Plan was born.
The Piper Plan is a document, unique to every person in the organization, that allows them to outline their ideal career path — and nothing is off limits. It quite literally asks the question: “What do you want to do?”
Based on these documents, we know whether or not the talent we need for new roles already exists in the organization.
Since then, it’s taken on a life of its own and grown into an entire Talent Development department. More on that later.
Our team motto is: We engage, hire, and develop the best talent in the world.
Above all, we’re about humanity first, with everything else built around it. At every step of our employees’ journey — engaging them, hiring them, developing them — we want to make sure we’re focused on them as people.
Which leads us to why we have to structure our team in a specific way.
Here’s a look at the current structure:
Talent is our core recruiting department. The reason our talent team is special is that they’re recruiters backed by an Ops department.
Why is this unique? Because it usually only happens at companies that are 1000+ people. But we knew we wanted to invest in Recruiting Operations and People Analytics in a more meaningful way.
So we did it at 100 employees.
En-Szu, our Manager of Talent Operations, has built a robust recruiting tech stack to make our team mega-operational and data driven.
Here’s our current recruiting tech stack:
This means that our talent team doesn’t need recruiting coordinators — we just have really amazing recruiters who are backed by systems that do the admin work for them.
This allows our recruiters to double-down on our human-first approach to talent acquisition: building relationships and providing excellent candidate experiences at scale.
In addition to Talent, En-Szu also built out our People Analytics and Operations. This department covers everything from headcount planning to compensation philosophy to People processes.
The fact that our people department functions as data-driven as most sales and marketing departments is by design. ‘People’ should get the same strategic support as other teams.
So why doesn’t every company do this?
Unfortunately, a lot of companies think the way to solve problems is to throw bodies at them (ie. make hires for everything). We see it so many times, and it never ends well.
Companies that scale irresponsibly wind up in situations where they have too many people, or they haven’t had the growth they’ve anticipated, and end up cutting a large number of their workforce to make up for it. Layoffs occur.
That’s the wrong way to grow an organization.
The smart way is to hire someone strategic who can put systems and processes in place that make the need for admin work completely obsolete.
Then, instead of spending a ton of money on an administrative role, you spend a tenth of that on a tool and take that cost savings and apply it toward a senior hire that can actually move the needle for your organization long-term.
Another reason why Ops is important?
Companies say that they’re passionate about DE&I (diversity, equity, and inclusion), but if they don’t have a strong people analytics function, then everything they’re saying is lip service.
Because if you can’t measure it, then you don’t know what you’re driving. You don’t know if you’re actually moving the needle for URGs (under-represented groups).
Hear En-Szu talk more about it here.
As I said, we believe in humanity first at Chili Piper. In fact, we have an entire department dedicated to the experience of being a human being here (aka. a Piper).
Hallie, our Senior Manager of Employee Experience, has built a department responsible for creating a seamless experience from the day Pipers sign their offers to the day they leave our organization to reach new heights.
We accomplish this (surprise, surprise) with lots of tools and systems.
Pipers get robust onboarding communication flows (thanks Greenhouse), welcome packages when they start work (thanks Sendoso), personalized & ongoing training (thanks WorkRamp), and they can even tell us exactly how they feel about all of it in regular engagement surveys (thanks CultureAmp).
Our commitment to growth for our Pipers runs deep. Our co-CEO Nicolas sums it up well below:
“At Chili Piper, our SDRs have the choice to go and work in any department afterward. We strongly encourage our SDRs to change. We have SDRs who’ve become product managers. SDRs who’ve become customer success reps. SDRs who’ve become event managers. We have no restriction on the possible path.”
So how do we make sure that our team, SDRs included, get on the right path for them?
Enter Nalani, Director of Talent Development and Coaching.
Nalani built a team of accredited Talent Development coaches who partner with Pipers, own Piper Plan conversations, and drive outcomes that benefit Pipers and, by extension, our organization.
This needs its own section to talk about.
When companies think about their People function, there are a lot of different schools of thought.
There’s the old school, “HR” mindset which is: Humans are a resource that you can manage just like any other resource in the company — financial or otherwise.
Fundamentally that’s not how we view things at Chili Piper.
When building our people department, we’ve taken great care to make sure we’re empowering the human beings that work here as opposed to empowering the company.
If you genuinely empower people, and it’s your primary agenda as a People department, then the company will profit — there’s no way it can’t.
Not only does it help us from an attrition standpoint, because we genuinely invest in employees and they want to stay, it means that our teams benefit from humans doing the best work of their lives.
This brings us to the difference between learning and development.
Historically, People functions treat L&D as one thing. One department. But at Chili Piper we believe that human beings are on a development journey, and performance is not about people.
Learning (synonymous with training) is specific to the role in which people sit, whether it’s a marketing role or an SDR role — and that falls under Employee Experience.
Development is how people can grow as human beings — and that lives under the Talent Development department.
The reason why that distinction is important is that when employees are underperforming in their role at companies that treat humans like resources, it becomes about the person not being good enough.
We don’t view it that way.
We view it as: The person is good enough (every human is), they simply might not be in the right role for their skillset which is why their performance might be lacking.
That’s why I put so much emphasis on aligning the person to the right role, and why there’s a whole department around development.
So why exactly do learning and development have to be separate?
Because performance conversations can be very sensitive. And when that sensitivity is anywhere near development conversations, which are inherently vulnerable, it can be problematic.
For example, we have Talent Development Coaches at Chili Piper: the full-time, accredited coaches I mentioned earlier whose sole purpose is to partner with employees on their developmental journey.
If there was ever a space where an employee was having a “performance issue” like not hitting their quota, and they take it to their development coach for help — this person who knows their deepest darkest secrets and aspirations — if that coach has any hand in the employee's performance review, it fundamentally alters the relationship.
It means that you can’t have that trust that’s critical for your own development. Which is why we take great care to separate the two.
Getting to this point didn’t come without challenges and mistakes.
If I were to give myself advice, there are some things I would do better. Unfortunately, I can’t go back in time, so I’ll settle for imparting my wisdom on you.
Progression App is our career development tool. It’s an awesome tool, but the tricky part is building out the skill frameworks for every single role.
The progression maps, which detail how to get from point A to point B in your career, took a very long time to create.
How could I have done that better?
First, I would’ve done a better job of getting buy-in — company wide — on why it was important before embarking on this journey.
I was fortunate enough to have Nicolas and Alina on board from the jump, but it was a matter of convincing other departments along the way. Asking managers to build out their team’s progression framework turned into an ordeal and took a lot of reminding.
If I could go back, I would’ve approached it as, “look at the amazing ways you can take advantage of the talent you’ve already hired! And you don’t have to sift through resumes or sit through interviews all day long.”
But I didn’t do that. 😅
And while now everyone is very thankful for it, at the beginning… it was a lot.
Initially, when I thought about talent development I just thought we needed someone to manage the Piper Plan initiative.
Now that we have Nalani, our Director of Talent Development and Coaching, on board, it’s become clear that there’s soooo much more to talent development than just Piper Plans.
It’s an entire coaching, leadership development, and strategic partnership department — and I would’ve started that sooner.
Maybe not the most surprising thing, but the most serendipitous thing that’s allowed a lot of this is that Nicolas and Alina are very much tool people. They’re software people. In fact, Nicolas doesn’t believe in hiring any administrative roles at Chili Piper.
Initially, that horrified me.
But I quickly realized he had a point. And part of the reason this structure even exists to begin with is him telling me, “You’re not going to hire a recruiting coordinator.”
So I needed to figure out an alternative.
The best way to do that was to invest in Recruiting Ops. I had seen how efficient it made other companies, and I didn’t have a choice but to be efficient. Luckily, it all worked out and ended up being really amazing.
The other thing I’ve learned?
It’s really possible to build a people-centric department that still relies on systems and data — two things that don’t seem inherently people-centric.
The fact that you can use software and numbers and math (see, kids? You can use math in real life!) to actually benefit human beings is pretty amazing.
Historically, HR departments have been known for scary things like, “We have to save money — let’s cut benefits here and do this there.”
But when you use the same math to show why it’s valuable to invest in employees, that’s the good stuff.
If you want to build out a human-first team, you’ll likely need some tools to get started.
If I had to rank our tools for how much we love them, it would be:
Tyler Parson is the Vice President of People at Chili Piper. She is passionate about building a company that empowers its people to show up authentically, do the best work of their lives, and learn from one another. Outside of work, you’ll either find her traveling, reading, or putting together one of her 125+ LEGO sets (seriously). Connect with her on LinkedIn.
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