Fast Access to Earnings: A Strategy for Winning and Keeping Gig Workers

During Shift Work Summit, challenges associated with delivering high quality payments solutions were top of mind. Shift workers depend on reliable payments as a key component of their financial stability. Chris Hollindale, Head of Checkr Pay and Akshay Rawat, Senior Staff Software Engineer and Founding Member of Checkr Pay discussed how flexible and fast payment systems help retain workers and improve worker satisfaction. They also highlighted the limits of legacy payment methods and explored how embedded finance is a comprehensive solution that can meet the new requirements of the growing gig economy.

Read the transcript following the key highlights below.

Shift workers have specific payment requirements (7:38)

Innovative payment methods provide long term benefits to workers (11:07)

Embedded payments for shift workers can be easy to implement (18:16)

Tech teams can provide flexible payment solutions without complex development cycles (21:47)

Gaurav Deshpande: Hey! Welcome, everybody! Welcome back to Shift Work Summit. I'm your host, Gaurav Deshpande, and we're ready to dive into everybody's favorite topic—getting paid highly. Shift payments are important for all workers, especially important for gig workers who depend on the money for their daily necessities from ride sharing to on-demand apps to now shift work marketplaces. Checkr has become the industry standard for background checks for gig workers. Many of you in the audience use Checkr here for verifying new 1099 workers as part of the worker onboarding when you're onboarding those to your marketplaces. Their Checkr Pay initiative lets you pay those same workers instantly.

With that I would like to welcome head of Checkr Pay Chris Hollindale and his tech co-founder, Akshay Rawat, to share more details about it at the Shift Work Summit—Chris and Akshay over to you.

Chris Hollindale: Thank you so much, Gaurav. Hi everyone, thank you for taking the time today. So my name is Chris Hollindale; I'm originally from the UK now in San Francisco where I lead the Checkr Pay team at Checkr, and we're excited to tell you more about Checkr and Checkr Pay shortly.

Just a quick intro to myself before Checkr; I spent 10 years in the food delivery industry, co- founded a company called Zesty which delivered food to companies. We later sold Zesty to Square in 2018 and we joined the Caviar team there, and later on Square sold Caviar to DoorDash. So I spent several years running a couple of product lines at DoorDash—lots of experience in food delivery and the gig work industry.

And with me today is Akshay; if you want to introduce yourself as well.

Akshay Rawat: Hi! It's exciting to be here. I'm Akshay, our lead engineer at Checkr; I live in San Mateo and work from Checkr’s San Francisco office before Checkr Pay; I was the founding engineer at a startup called Clerkey and co-founded a couple of companies before that—back to you, Chris.

Chris Hollindale: Awesome! So you may be familiar with Checkr as a background check company as Gaurav mentioned—we founded in 2014; today we have over 800 employees and over 100,000 customers and we service 95% of the background checks for gig customers in the U.S.

Needless to say, we spent hundreds of hours talking to gig companies and understanding their needs and pain points—and that was how Checkr Pay was formed.

Through our customer research, we learned that payments are critical to success for anybody who employs flexible workers. Checkr Pay unlocks instant payments for your flexible workforce; we offer several different payment methods in one package which includes direct deposit, instant direct deposit, and truly free instant payments through debit cards.

The whole experience is embeddable and co-branded to your company and it's a full-service offering which we think is very important—and we'll talk more about later in the session.

It also includes a revenue share program that allows you to turn your outgoing payment stream into a source of revenue for you and your company.

So before we get started I just want to talk a little bit about how we fit into the conference; at the highest level of shift workers' lifecycle can be distilled down into three main stages—pre-shift, on-shift, post-shift.

Before a new worker starts their first shift they have to be screened—and that's where Checkr comes in at the very beginning with its commonly known background checks product.

Once onboarded they need to be allocated assigned or choose a shift—and that's where today's host HyperTrack comes in; that location intelligence platform allows you to make sure that the work is gonna start on time alerts you if they're going to be late potentially or be potentially be a no-show—and it also provides verification when they leave and facilitates payment based on clock-in and clock-out.

Finally once it's approved the shift earnings are then paid to the worker—and that's where Checkr Pay comes in.

All of these linked experiences are where these parts will work together seamlessly; today we're mostly going to focus on this last step and ensuring that we can get to that last step as quickly and efficiently as possible.

So just quickly what are we gonna touch on today? We'll start by just talking about the gig economy in general and flexible work—the growth and challenges there—we'll talk about how we can solve some of those challenges with embedded finance solutions—we have a real customer example—and we may or may not have time for QA—we'll see how it goes.

Cool! So our session's called fast access to learning—a strategy for winning and keeping gig workers—and first of all, to understand why instant payments are pivotal in that let's first recognize the growth of the gig economy.

Today 36% of U.S workers are employed as independent workers—which is over 57 million people; by 2027 projections indicate that over half of the U.S workforce will have engaged with gig at some point—and noticeably between 53% of those between 18 and 34 rely on gig work as a primary source of income.

This is a market that's large and expanding—and the linchpin to gig economy success is its supply—its workers—as I mentioned I previously worked at DoorDash and I've seen how many people have been Dashers in the U.S., and the numbers are staggering—this is large and not going away.

We're not the only ones who have noticed this growth; businesses have realized this opportunity—and there are now Uber-for-X services in every category imaginable—as a result of that gig workers have more choice of companies than they've ever had before.

With that accelerated growth companies face two interconnected challenges—increasing competition as well as attracting and retaining workers with those competitive companies.

Shift workers have specific payment requirements

“Financial health plays a huge role in decision-making for this population—and can be deciding factor as to where they choose to spend their time.”

If we turn our attention to the workers themselves they face many challenges—financial burden and financial uncertainty is huge one—and drives the majority of decisions for gig workers; 70% of gig workers have less than $1,000 in savings—and over 40% have no savings at all—so it's a huge deal for them.

Lack of benefits is another challenge—in particular this population is often underinsured and lacks a good safety net—and they can often be what we call underbanked—they traditionally lack good credit and access to financial systems in general—in our discussions with some of the largest gig companies this is a common problem that affects a large minority of their workforce.

The result of all these problems is that financial health plays a huge role in decision-making for this population—and can be deciding factor as to where they choose to spend their time.

To put some challenges into perspective here are some recent studies that emphasize impact finances on shift workers—financially stressed workers are two times more likely look for another job—76% prioritize instant access payments ensure stability—and 85% would work more often if they were paid much faster.

While I'm using term gig here these challenges are not unique just 1099 workers—this impacts all flexible workforces—the healthcare industry is great example many companies use W-2 classifications flexible nursing positions regardless they're all competing against each other for same pool workers—these are key decision-making criteria people involved.

As company what can you do help solve alleviate some challenges? The most obvious answer—you can pay people more—but while that's simplest answer it's not really an option most people—we're all budget constrained tasked growing gross margins profitability once you've raised compensation number it near impossible bring back down—so this usually best solution problem—but there are some realistic alternatives—you can give money access faster—this really split into two parts—it can process submit payment faster first place—and then once it's processed submitted can transmit it faster.

Secondly—you can give flexibility how where they receive money—ifferent workers have different needs, and the higher flexibility you give them, the larger percentage of the population will be happier.

Thirdly, you can help them stretch their dollar further. For every dollar you pay them, how can you make it go as far as possible? Examples include cashback programs, perks, discounts, and other ways to stretch the money you already pay them. These are the three key goals you should have for payments for your team. As we go through the rest of the session, keep these in mind as key evaluation criteria for what a good payment system should look like.

Innovative payment methods provide long term benefits to shift workers

“Our perspective is that full-service embedded finance is the single solution that helps address workers' financial needs. This allows any company to integrate banking and financial services, changing how they pay and engage their workers.”

Part of the challenge for companies today is that we're continuing to use legacy payment methods that do not solve these problems or meet these standards. Methods like cash, checks, and slow ACHs fail to address the outlined problems. They are slow, inflexible, and generally require workers to have an existing bank account. They’re inconvenient and offer no benefits to help stretch a dollar further.

Our perspective is that full-service embedded finance is the single solution that helps address workers' financial needs. This allows any company to integrate banking and financial services, changing how they pay and engage their workers.

Properties of this solution include: it must be fast and easy to integrate; it should work for both the company and workforce without needing expertise in banking or customer support; it should offer multiple payment rails for flexibility; and it should be embedded into existing apps for better adoption and engagement. People now demand clean, frictionless experiences, similar to one-click payments on Amazon. Fintech has come a long way in providing such experiences.

Workers are increasingly comfortable using digital wallets or banking services without physical branches. Instant payouts through solutions like Visa Direct and Mastercard Send are becoming standard. FedNow is another faster payment rail expected to gain adoption over time.

With that, I’d like to hand it over to Akshay, who will provide a deeper dive into specific challenges and how full-service embedded finance solutions address them.

Solving Challenges with Embedded Financial Solutions

“Our two broad goals were: reducing payment frictions for everyone (workers to customer support teams) and enabling creative payment experiences that drive worker engagement during pre- and post-shift phases.”

Akshay Rawat: Thanks, Chris. When building Checker Pay, we focused on understanding payment problems faced by high-growth customers. Many customers use "time to first payout" as a key metric because it measures product success and operational efficiency.

Our two broad goals were: reducing payment frictions for everyone (workers to customer support teams) and enabling creative payment experiences that drive worker engagement during pre- and post-shift phases.

To reduce time to first payout, we need to focus on payments KYC and onboarding in pre-shift phases to reduce fraud. A common issue is workers re-entering data already provided during background checks when onboarding for payments. This delays payouts.

Solutions include integrating background checks into onboarding processes (e.g., Checker Pay supports one-click KYC verifications) and offering self-service corrections alongside human support options.

Another challenge is meeting workers' payout preferences. Workers often switch between payout methods depending on urgency—e.g., direct deposits for non-urgent needs versus instant push-to-card transfers when needed immediately. Building each payout method in-house is costly due to varying technologies, speeds, fees, and dispute policies.

Embedded payments for shift workers can be easy to implement

A single experience offering multiple payout methods managed by one provider can address this challenge. Options include ACH direct deposits (slow but low-cost), push-to-card transfers (instant but with fees), or branded debit cards (instant transfers with cashback benefits).

Integration has become easier with no-code solutions for bulk payouts or embedding wallet experiences into mobile apps via APIs.

Barriers to instant payments often include shift verification needs and cash flow issues. Shift verification involves validating completed shifts quickly using automation or signals like worker history or MVP programs. Flexible flows can also allow workers to request portions of their wages based on custom rules.

Cash flow visibility issues can block instant payments if companies must pay workers before receiving their own funds. Solutions include low-balance alerts, shortfall fund transfers, or integration with third-party lending services like Oatfi.

Tech teams can provide flexible payment solutions without complex development cycles

Scaling payments can be costly due to manual processes like resolving disputes or chargebacks. Full-service embedded finance solutions minimize costs by integrating KYC technologies, offering self-service features (e.g., chatbots), and providing transparent dispute resolution processes.

These solutions can also generate revenue through interchange fees from custom card programs or faster payout fees while offering benefits like tax filing partnerships or cashback programs.

Chris Hollindale: Thank you, Akshay! Let me share an example of Labor Jack—a labor marketplace based in Fort Collins, Colorado—that successfully implemented Checker Pay’s full-service embedded finance solution.

Labor Jack faced challenges like high competition, delayed payments (over two days), and insufficient worker support from their previous vendor. Their solution included seamless integration of background checks for faster onboarding, instant payment systems reducing delays, worker rewards programs (cashback/safety net benefits), and automated tax filing processes.

Outcomes included a 35% reduction in onboarding time for new hires, a 5–10% increase in retention rates, and immediate payouts after shift completion instead of weekly cycles.

Key takeaways include recognizing payments as critical to workers’ day-to-day decisions; leveraging full-service embedded finance as a strategy for attracting/retaining workers; implementing embedded payments easily; and choosing solutions offering flexibility with minimal implementation effort.

Gaurav Deshpande: Thank you both! We’ll now move on to another case study about daily payments for W-2 workers. See you there!