Ep. 99 – Checkr Chief People & Operations Officer, Linda Shaffer

Background checks will never be the same, thanks to Checkr, a SaaS company that revolutionizes the background checking process by harnessing the power of artificial intelligence to process data impartially. A far cry from the extremely tedious and antiquated processes that has so far characterized the background check industry, Checkr makes it its mission to raise fairness in the process through technology. Leading the company’s Operations, G&A and People is Linda Shaffer, who has served in various leadership posts within the company since its startup days more than four years ago. Wielding her extensive experience in growing data products, developing scalable operations and managing teams, Linda is a perfect fit for the fast-paced technological space that Checkr is swimming in. Join in as she shares the unique challenges and rewards of working in this disruptive company in this conversation with Cameron Herold.


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Linda Shaffer manages Checkr’s operations and is committed to building the highest level of quality service for customers and applicants. She’s successfully scaled operating teams in fast growth, data-intensive companies in media and telecom at Yellow Pages, Sense Network, Nielsen and Accenture. Linda leads operations in G&A and People at the SaaS startup, who has modernized the background check. She has an extensive line of experience commercializing and growing data products, developing scalable operations, and managing teams in both small and large operations. This focused on growth companies scaling from startup to growth, data and analytics businesses. Linda, welcome to the show.

Thank you, Cameron.

I’m looking forward to learning from you. Why don’t you give us a little bit of your background or a little bit of a helicopter tour? Maybe walk us through where you gained some of your experience and walk us through your bio so we get a better understanding of you and your skillset.

I started out early in my career exploring where I should go. I landed in the energy industry in my early career. One of the things I appreciated about my path from my early days is to check that I’ve had the opportunity to work in a large number of industries in a variety of personal capacities. After I started off, I was working at a utility planning energy efficiency programs for hospitals and schools in New York State. I came to the early conclusion that working inside a public utility was not quite the pace I was looking for in my career. I decided to venture which for a girl from New England from the East Coast was a big change of pace. I’ve never looked back since that first move out here. It was a little bit of a lurk to move out to California at the time, but it has been important in my trajectory in Silicon Valley as well. After those early days in the energy industry, I went back to business school. I ended up working at Accenture, which was a great place for me to develop broad-based business skills and get exposure to many different industries.

I was working in the strategic consulting group there. I did that for about two years until the travel wore me down as it does for many people. I landed at a startup in San Francisco called Telephia, which was a market research company focusing on the wireless industry that was later bought by Nielsen to build out their telecom practice. It was an important role for me and my development. When I look at my roles that I’ve had since then, I’ve been trying to replicate that experience that I had at Telephia. It was a textbook startup experience. We were introducing a new product in a new industry. I started on the product team and spent about seven years in a product management capacity, which helped me understand the business.

It was a leap of faith that I switched from leading product teams over to leading operations teams. My boss called me on the phone. I was on maternity leave at the time and said, “We have this opportunity we think would be exciting for you. What do you think about running our operation?” Operations at a data business are often messy because all data businesses have a secret where there’s always some manual work happening in the back office as even as much technology and automation you can compare. There’s always a human element that needs some process and rigor. That was my first role in applying what I had learned about business to an intensive operational role. I’ve leaned that way ever since then through the rest of my career at Nielsen, later at Sense Networks, and now here at Checkr.

When you did the jump from product to operations, you said they were very different, what were the big differences? What did you have to learn or unlearn?

The biggest thing I had to learn was how to build a repeatable task at scale. Working as a product manager, the work is more project-based like you’re dealing in general with higher-level business concepts. You’re working with teams that are highly skilled. Working in an operations role, the job has been more of how do you take a problem that you’re trying to solve and break it down in a way so that it can be executed by a team often a large team over and over again with high levels of consistency and accuracy. Build those processes in a way that doesn’t rely necessarily on the intellectual horsepower of the individual. It’s more about building the right system.

That was a different challenge because previously, my problem solving relied on the capacity and quality of the product managers that I hired and their ability to make good business decisions. It was less systematic. That was the biggest shift. There were all other problems that I had to deal with that I never had encountered in a product role. For example, one of the products that I led the operation on was a network testing product, which had vans that we would drive all across the US to benchmark the relative quality of different wireless networks. Comparing like Ryzen to T-Mobile and how clear were the phone calls and did they drop your call? That business was operationally intense. We had vans that were driving all across the country, they would hit snow storms and the drivers would get detained. There was a different set of challenges that I faced on a day-to-day basis that sometimes surprised me like the things that would happen on the job.

You’re dealing with a lot of stuff that’s out of the box and more of problem-solving. I’m not winging it. Are you having to be more reactive in some of the areas of operations than you were on the product side?

Probably in part especially, early on in the role because it was new to me. Overtime figuring out how I could bring my planning skills to the team to help them be more proactive and anticipate issues. We know it’s December in Minneapolis, so we know we’re going to have delays and how do we plan that into our program. It took some learnings to get there.

It’s astounding to me though, how many companies don’t take time to be strategic and think strategically. That is thinking of seasonality in a certain market. It’s amazing that some companies don’t do that. They operate under general flatline assumptions and they don’t think through those things. If you’re in a fast forward, you grow things. If you’re over at Checkr, you’re running operations, their chief people and operations officers, tell us a little bit about what Checkr does and then what your role entitles?

We are a background check company. We do pre-employment background checks as well as post-hire monitoring and risk mitigation for companies. We have been a big disruptor in this industry. The company is a few years old and we were started early on with the recognition that the background check industry as a whole was extremely antiquated. The legacy companies that were predominant at the time had relied a lot on manual processes. They weren’t tech companies and they were not tech-forward. Many of them at the time did not even have APIs that more modern companies could integrate with. We sought to apply automation and artificial intelligence to the entire process so that we could deliver not faster and more accurate background checks, but also help reduce bias in the hiring process.

SIC 99 | Checkr CPOO

Checkr CPOO: The operations role entails building processes that can be executed by a team over and over again with high levels of consistency and accuracy.


Who are your target clients?

Checkr grew up in a gig economy. Many of our customers like Uber and Lyft. Probably about 95% of the gig economy are Checkr customers, but we also serve more traditional enterprise companies as well. It happens that almost all of the 10 million jobs that were created since 2005 are temporary gig economy jobs. That’s where the growth in the economy has been and our business has been historically focused.

Your role there at Checkr now, chief people officer, chief operations officer. Walk us through the business service that you run. What doesn’t report to you?

I run the people team. Our talent and people operations team, our legal team as well as what we consider to be internal operations, which is any part of our internal process that requires human intervention. I mentioned a Checkr that we’ve done a lot of automation. These teams relatively speaking are not big. They’re all in San Francisco and Denver but those teams are doing quality control on reports that we think need extra diligence either because of severe crimes or we know there are some known edge cases that our system wasn’t designed for. They also handle any candidate question or dispute that might come up after the background check has been delivered. Candidate support teams, quality teams and research teams that are deeply versed in the nature of our business.

You report to the CEO. Who else reports to the CEO?

I report to the CEO. We have a Chief Business Officer who handles the revenue side of the house for sales marketing and customer success groups. We have a chief financial officer who handles finance and strategy of the company. We have a Chief Product Officer who is responsible for product engineering, our trust and security teams.

Can you give us an example of a scope? Can you talk to us about how many employees you’ve got full-time and part-time where people are operating?

We have about 600-plus employees in total across all of our businesses. In terms of my scope, I have about 135 of those people.

What was it about the company that you liked when you joined? What size was it when you got involved?

I joined Checkr a few years ago and the company was about 60 people. I had closed our series B funding. We were growing like gangbusters. The company needed help in scaling operations and bringing consistency, rigor, and keeping up with a piece of our business growth. I was attracted to Checkr because one, it was a good match for my prior experience both in operations and in working with products that were data-based like market research product, the data you’re delivering. It was a good fit for the industry. I also loved that it was this like unsexy corner of the technology world that had not been disrupted and having come from advertising or working more with consumer advertising. I found this to be interesting.

Dovetail into your product side, engineering side and operations. You’ve seen a ton of growth from 60 to 600 people in four years. Not a lot of people would go through. Would that be 3 doubles, 4 doubles, 60 to 1 20 to 240, almost 3 or 4 years of 7% growth? What did you learn through all of that? What changed?

Almost everything has changed. One of the things that have kept me excited and engaged at Checkr is that it feels like I’ve worked at a different company every six months because those changes were dramatic. Early on, when I first joined Checkr, my personal role was hands-on in the operation and close to the details of how are we setting up Zendesk and exactly what metrics are we using to track our operation. Over time, my role has changed to be more strategically thinking about what do we need to do to maintain culture of the company as we’ve grown so much. How do we hold onto our core values? How are we making sure the communication and the company are staying clear and robust as we have hired many people. One thing that has been in common across that whole period is I have consistently done a lot of is interview. I’ve done 600 or 700 interviews. Hiring has been one of the most important ways that I have an impact on the company is who I bring in to lead teams.

I’m going to go back and ask you about some of the growth stuff, but I want to ask about the interviews because I’ve been talking about it all day with a couple of my clients. What do you think are the biggest or the best areas that people can go to gain some skills in interviewing even to get them, if we were to say to a bronze, silver or gold skill level just to get some basic good competency? Where would you point them?

SIC 99 | Checkr CPOO

Checkr CPOO: Head of People is a more holistic term that encompasses not only the technical side of complying with HR laws and practice, but more broadly thinking about building a company culture.


Practicing out loud is one of the most important communication skills that people can do on their own or with a friend.

I’m talking the interviewer.

The interviewer to get skills is a good question.

Most people have no idea how to do a job interview.

One of the things that’s been unique about Checkr is that we have had a structured interview process from the early days of the company. That has helped us onboard managers and new interviewers, who had never thought about how to ask good situational questions for people and how to structure the interview in a way that makes sure that you get out of it. What you’re trying to evaluate, whether it’s core values or the capabilities of the job. I don’t know. I have to think about that one.

The company had a process and a system in place and you made sure people followed that. It sounds like that.

We had a process and a system. As much as we have tried to eliminate bias in hiring for our customers through our products, we’ve tried to do that ourselves with our own hiring processes. Both in terms of the structure, the design of the interview panel, who’s interviewing and making sure that we ask a consistent set of questions to the panel. We’re truly assessing the skills that we need for the job but also in terms of diversity, we have a requirement for our teams to interview at least two diverse candidates before they make an offer. This isn’t helpful for people to build this from scratch, but defining structure and trying to encourage consistency and interview process is important.

That’s a huge point that most companies don’t have that either. One thing that I don’t understand on the interviewing for diversity, I spent a full day inside of a Maximum Level Four State Penitentiary coaching prisoners. I was astounded at some of the biases that we have where prisoners will never get a job. When they get out of prison, nobody is ever going to hire them. Do you guys, being in the background search company, have anything that you proactively do to try to help prisoners get jobs when background checks are going to be biased against them?

We do a lot. Our company’s mission is to build a fair future and we understand the challenge that people who have a criminal record face in employment situations. One thing I didn’t know a lot about before I joined Checkr was our criminal justice system. I’ve learned an incredible amount, 1 in 3 Americans have a criminal record that can prevent them from employment. Employment is the single biggest influence on reducing re-offense. It is an important piece of it. We have built into our product tools that help hiring managers to reduce their bias in hiring by not even looking at records and their adjudication process that might bias them.

One common example of this is marijuana in California is now legalized. If a hiring manager doesn’t want to see those records at all even though they’re technically reportable on the background check, we have software tools that make it easy to do that. It’s foundational to do both how we think about building products and how we do our own hiring. We ourselves do fair chance hiring here at Checkr. We set specific hiring goals for what percentage of our company we want to be fair chance. We target more than 5% of the company and it’s our goal as a whole company to be leaders in fair chance hiring in the US. We’re active in the fair chance hiring community.

Sorry, that was a loaded question that I didn’t intend to ask it in a confrontational way, and I’m glad you guys have. It’s something I’ve been thinking a lot about. I’m curious about something. I was talking with the founder of Infusionsoft about this. He and I both have a metric in place related to growth that a senior leader can only ever go through two consecutive doubles in the size of the company before their role is at risk. How did you guys get through that? What do you think it was that you did to go through three doubles now in terms of employee size? Ben Horowitz in his book, The Hard Thing About Hard Things, that a leader can only go through one triple. How do you get through that? How have you continued to scale at Checkr so that your skillsets continue to grow and you’ve adopted?

It hasn’t always been easy. To that point, we’ve had a fair number of leadership changes over my time here. I’m one of the longest-tenured executives for the reason that you’re saying that people often have a sweet spot in the doubling. For me, what has helped is that I’ve always been willing to take on new areas of experience that I did not have maybe a proven track record in. For example, most of the people team that was a new ad for me, I had not previously led that part of a company. My own willingness to take risks, not to do what I had already done and what I already knew has been important. I think building a strong relationship with our CEO. He trusts me and is willing to also take some risks with what he’s willing to give me.

I’m going to go there because it’s critical for any of the second commands and CEOs that are reading. I want to go back about with your role as taking on as being the head of people is one of your core roles. It seems to be a movement over the last number of years. We were the same when I built 1-800-GOT-JUNK. We hired a woman who had been the head of people at business objects and crystal decisions. She came into the HR head of people. It was a cognizant term that we used instead of calling her the head of HR. What do you distinguish is the difference between the head of people in the head of HR? I’m curious as to what your take is on it.

SIC 99 | Checkr CPOO

Checkr CPOO: Every time you bring in a senior leader or any leader, it has ripple effects, not on the team they’re leading, but all the teams around it.


When people use the terminology, HR, it has more functional connotations versus thinking about the entire Lino lifecycle and experience of employees and people at the company. I see it as just more holistic term that encompasses not the technical side of making sure that we’re complying with HR laws and practice, but more broadly thinking about the culture that we built here at the company in many ways like the brand that we have in the market.

What you discussed was considering the impact on the whole life cycle of the employee versus policies and procedures. That was the way we looked at it as well was someone to sit and think about the impact of everything we did on the people. It was a big-wow when somebody would, “how are we going to explain that to the people?” We’re like, “I don’t know, we hadn’t thought about it.” “What’s this going to mean to their day to day?” I was like, “Can you think about that either?” It’s a powerful role when the head of people sits at the leadership team table versus being relegated to the corner like it used to be. The other thing I wanted to ask about was dealing with leadership change. When you have some transition in here hiring, as you guys have had to do for sure in your growth, when you go from 60 to 600 people, you’ve had to bring in some outside senior leaders into the company. How do you bring in those senior leaders successfully? What do you think works to do that successfully versus unsuccessfully?

One of the most important things that we’ve done as a leadership team is continuously invest in building a strong leadership team. We’ve done that intentionally over the time that I’m here through more formal practices. One is that we’ve had a strict operating cadence of when our most senior team meets and how we meet. Historically, we’ve done at least stand-ups with the most senior leadership team where it’s fifteen minutes a day and we’re connecting and talking about the business. As well as structured weekly tactical and strategic meetings so that we have an operational rhythm to how we’re working together. Every quarter we go offsite as a leadership team for two days. We spend time talking about the health of our team and giving each other feedback about unproductive behaviors that we’re seeing or fact about our teams. We invest the time to get to know each other and build trust on the team which we believe that if you can have that foundation of trust at the most senior team in the company, that is an important foundation to performance and results across the whole company. If you have a dysfunctional leadership team, it’s very hard.

It goes back to Patrick Lencioni’s The Five Dysfunctions of a Team, the absence of trust, the fear of conflict.

We worked closely with the table group. We drank the Kool-Aid on that.

Another question when you’re bringing in a senior leader into the organization, what ripple effects do you see that sometimes people don’t notice, some of the unintended ripple effects of bringing in a great senior leader. What do you caution us to look at when we’re doing that?

Every time you bring in a senior leader or any leader, it has ripple effects, not on the team they’re leading, but all the teams around it, like our CEO and how he does his job especially being in a fast-paced startup. All of us have played pinch hitter in many different roles in the organization. As you bring in the right leader for the right time, that requires flexibility among the rest of the leadership to adapt and adjust, to give those leaders space and runway they need to do their jobs. We have a new CFO and new chief product officer here at Checkr in the last few months. That changes our team, my role, our CEO’s role, and how we’re all operating.

Talk about the relationship with the CEO because you mentioned that was something that you’ve worked on to build that relationship. That’s been key for some of your longevity and also growth with Checkr.

One of the things I love about our CEO, Daniel, is that he is incredibly open to feedback and very self-reflective. That has been an important ingredient in us building a successful relationship because I know that if I give him feedback, he’s going to listen and take it seriously. As a first-time CEO, understandably, there are lots of areas that are going to be new for him. It’s not just helpful, but it’s important for him to get feedback from someone who has experience in different areas. One of the key things in me building a strong relationship with Danielle was me being honest with him about challenges I saw in the organization, the company, or the business and bringing those things to him even when it was hard.

You’re touching on an area that a lot of senior leaders are very uncomfortable with and it’s that fear of conflict and radical honesty. We can all read and watch videos on it. At times, it’s hard for people to practice. walk us through a specific example like, “This happened. This is what I had to tell them. This is how it went.”

This is common for startup CEOs who cared deeply about the business. Our CEO is our first product leader involved in many parts of the business. As his leadership team has grown, he’s brought in a more experienced leadership team. It’s been important for Daniel to step out of some of those details so that his team can lead their areas. We’ve gone through a process where we’ve been trying to be diligent about reviewing hiring requests from our teams to make sure that we’re not spending too much money. Daniel has been involved in many of those low-level hiring decisions, not necessarily who is hired, but like, “Should we fill this particular position?” At some point, that’s not scalable for a 60% organization. We had a discussion with him where we asked him to step back from our backfill process and let us make the decision. He heard the feedback and we’re going to keep working on it. What’s hard about that for Daniel and for many CEOs is that he cares deeply about the business too. He wants success for the business, I don’t think he does it because he thinks he doesn’t have anything else to do. He does it because he cares about the business. We have to help him identify those times when the best thing he can do for the business is to step back and let other leaders take a shot at it.

I remember having that same discussion with Brian when we were building 1-800-GOT-JUNK and you identified the key point that he was struggling with, which was, he does care very deeply about the operation, people, franchisees, and the promises we’ve made. He felt like he was stepping away from that. What I had to let him know was I have every single best interest of his at heart as well, and if anything goes sideways, they can go around me to get to him. It’s a great discussion you have with them. What do you think you focus on in terms of the day-to-day, growing your people and growing your team?

What I focus on my team is trying to help them articulate for themselves. What are the things that they’re good at? What are they working on? What can I do to help them get access to the opportunities that they need into building their own skills? Whether that is someone who’s never managed people before, and how to help find opportunities for them to develop management skills. That’s a common interest among more junior employees. On more senior employees, it could be like, “How do I help them understand how to get exposure to more senior levels of the organization and more broadly influence in the org?”

It’s a gap analysis. Do you point them in the direction of self-work? Is there ongoing coaching and mentoring? Do you guys use outside resources?

It’s a combination. Ongoing coaching is my personal style with my team, but we have also worked with outside coaching like a company called a better manager for some of our first-time managers to get access to professional coaching sessions. We’ve started investing a bit in internal coaching on our people team where we have someone who’s starting to work with some of our junior managers and helping them get through some of the things that are hard for new managers like giving hard feedback as an example. We also did the executive level. We’ve been very supportive of executive coaching. I’ve used executive coaches, our CEO has, many people on our senior leadership team because it’s a practice that everybody can benefit from.

I get to the stage that all of us, “Every day we wake up, this is often the biggest thing we’ve ever built.” It’s the fastest-growing, it’s the newest change, or it’s the newest tech. It’s always stretching or promoting us for most great leaders. It goes back to Ray Kroc who built McDonald’s that said, “When you’re green, you’re growing and when you’re ripe, you’re rotting.” If you pick any sport, the best athletes in the world have coaches. All kinds of different coaches that growing ourselves is no longer negative. The school system taught us that getting a tutor it’s because you sucked at something. Now, it’s about getting a coach for what you’re great at. Do you work at building any of those unique ability teams where you try to get stuff off people’s plates and have them only working in unique ability zones versus coaching them on stuff they’re bad at? Any thoughts around that?

Not with any formal practice, but I’m a firm believer that people get advanced careers by focusing on augmenting what they’re good at, not just working on what you feel your weaknesses are. It’s like working on the muscles that are strong and developing a true exceptional ability versus trying to be peanut butter across everything.

How about yourself? Are you starting to look forward into the future for you? What do you think it is that you’re working on?

Some things that I’ve personally been working on is public speaking. An example of that is we do a big company offsite every year where we bring everyone from the whole company together. I was the ringleader. That’s been a new skill for me to practice communication in larger environments and learning how to have an impact on those communications in those kinds of venues. That’s been an interesting area of development for me.

I was at an event called The Cult Gathering. It was a number of chief marketing officers from some amazing brands that were all speaking to about 1,300 people in the audience and involving all these CMOs. It’s a cool group. Final question, if you were to go back to your 22-year-old self, what word of advice would you give yourself back then that now you know to be true, but you wish you’d known when you were moving to the West Coast or starting in your career?

Stop worrying, it’s going to be fine. I spent the early part of my career thinking more about like, “Was this particular decision, the right decision? Was this job, the right job? Was this company, the right company?” With the benefit of hindsight, I recognize that there are very few decisions that are irreversible and there isn’t any job or company that I haven’t learned something from, even if it was not the experience I expected coming in the front door. It’s being flexible and not sweating it out.

I often go back and think of my career, how I got to where I am at the number of little opportunities that turned into where I am now. I wonder what would’ve happened if I’d turned left instead of right. Not out of regret but more curiosity like, “If I picked door number one, who knows it’s crazy?” Linda Shaffer, the chief people and operations officer for Checkr, thanks very much for sharing with us on the show.

Thanks for having me on.

I appreciate it. That was great.

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About Linda Shaffer

SIC 99 | Checkr CPOOLinda Shaffer manages Checkr’s operations, and is committed to building the highest quality of service for our customers and applicants. She has successfully scaled operating teams in fast growth, data-intensive companies in media and telecom at YP, Sense Networks, Nielsen, and Accenture.

Checkr brings machine learning to the modernized process of background checks. Launched in 2014, Checkr has grown to over 400 employees with offices established in San Francisco and Denver. Their mission is to raise fairness in the background check process by utilizing artificial intelligence that processes data in an impartial way, highlighting only the best qualified candidates.

Linda leads Operations, G&A, and People at this SaaS startup who has modernized the background check. She has an extensive line of experience commercializing and growing data products, developing scalable operations, and managing teams both small and large. Linda is focused on growth companies scaling from startup to growth operations in data and analytics businesses.


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