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Jaime McDougall, Senior Director of Growth Program Strategy at DailyPay

Jaime McDougall: Driving the Wheels of Change in the Fintech Space

“The art of communication is the language of leadership.” – James Humes

The argument on what works for effective leadership has existed as long as there have existed leaders. Among all the numerous qualities that have been debated over to be imperative in a leader, everyone would be on the same page when it comes to the quality of having effective communication skills.

Perfect and precise communication is undoubtedly the most important trait that an individual in a leadership position must possess. The simple logic behind the emphasis on this particular quality is that effective speech is the outlet through which a person puts their message across. It has the power to make or break things. It can inspire and motivate people to achieve their personal and organizational goals at large. When utilized optimally, communication can drive the wheels of change in any given sector.

One prominent name among such leaders who have recognized the potential of this trait is Jaime McDougall, the Senior Director of Growth Program Strategy at DailyPay. Starting out as the Director of Marketing at DailyPay, Jaime climbed up the corporate ladder through her knack for innovation and creativity.

We at Insights Success caught up with Jaime in an interview to learn more about her professional journey in the fintech space and her approach to leadership as an individual.

Below are the highlights of the interview:

Jaime, please give us a brief overview of your journey as the Senior Director of Growth Program Strategy at DailyPay.

My path at DailyPay has always been on the marketing and revenue side of our organization. I started at DailyPay when we were direct to consumer, working with a lot of our customers – Uber and Doordash drivers – and building out an influencer marketing and referral program. I was intimately familiar with how customers viewed DailyPay, challenges in the buying journey, and the key strategies that drove acquisition.

When we pivoted to B2B2C, I led our inbound demand generation efforts attracting new businesses to our platform. I learned so much about how to communicate to executives the value of DailyPay. How DailyPay drives value by reducing turnover and improving employee engagement and recruiting, which has a direct bottom-line impact.

Marrying the two, I was best positioned to think about our go-to-market strategy for launching new DailyPay programs. I understood how we needed to communicate to companies and to the companies’ employees (our end customer). I created standardized launch playbooks to create awareness and consideration for DailyPay inside of our partner companies.

The B2B2C side of the business makes marketing to our end customer less straightforward than other consumer brands. Companies that we partner with vary in size, industry, and employee population, which all impact how an employee might learn or consider the DailyPay benefit. So, I am constantly thinking about creative marketing solutions for reaching employees of our partner companies directly. 

Tell us more about Dailypay, its offerings, and its stronghold in the financial services space.

At DailyPay, we are flipping the financial system by building a financial technology platform that starts working the minute work starts. Founded in 2015, DailyPay is the leading on-demand pay service provider that enables employees to control when they get paid.

The current payroll system is a failing system that keeps employees in a payment cycle that is dependent on their employers. DailyPay is challenging this old way of thinking by utilizing the Pay Balance to give employees their earned money when they want it while supporting businesses by designing uniquely tailored systems that are revolutionizing how companies pay their employees and interact with pay.

With our existing Pay Balance model in place, which enables employees to have access to their on-demand pay, we expanded our Pay Balance platform and built innovative solutions on top to efficiently manage pay transactions for employers, employees, banks, and merchants.

Forward-thinking companies across the U.S. turn to DailyPay to help them build a happier, more engaged workforce, which has become especially important as the U.S. economy recovers from the COVID-19 pandemic and subsequent workforce shortage.

Being an experienced leader, share your opinion on how the adoption of modern technologies like AI and ML has impacted the financial services industry and how is DailyPay riding the technology wave?

While companies have been investing in consumer-facing technology to stay relevant and to create a seamless experience for their users, many have neglected their own employees. With the ‘Great Resignation’ sweeping the country, many workers are now leaving for new opportunities and joining companies that invest in their people. As a result, many companies are seeking new benefits for their employees.

With finances being a top priority for many individuals, companies are searching and implementing the best financial technologies and benefits, such as on-demand pay, into the benefits package. The demand for new financial technologies continues to rise, and DailyPay has been garnering much attention in the process. From being mentioned in Fortune 500 businesses’ earnings calls to job posts to increase recruitment rates, DailyPay is a key benefit that many companies are leveraging to remain competitive. 

Considering the example of the COVID-19 pandemic, how do you plan to navigate through similar situations in the future?

The two words that come to mind are employee safety and flexibility.

Nobody likes the unknown. Communication and showing empathy in a time of crisis is the best thing a leader can do, as well as providing a two-way dialogue for employees to connect with each other and feel like the company is listening and has their back.

Employee safety has multiple meanings — physical safety, financial safety, and psychological safety. It’s the employer’s and my responsibility to ensure that my employees are taken care of in every way possible.

If the pandemic is affecting my employees’ health, I need to make the call for all employees to work remotely. If my employees are struggling to make ends meet on a biweekly salary, it’s about finding ways to give them access to their pay daily. If the pandemic is taking a mental toll, I need to make sure they have the healthcare necessary to get the medical attention they need.

One thing we’re still learning from the pandemic is to be prepared for the unexpected. So many companies have had to change their return-to-work dates and other company-wide plans because of new variants and rises in covid cases. If a similar situation were to arise, I would say create a flexible plan because you don’t know what might change.

What efforts did you take during the pandemic to sustain operations and ensure the safety of your team at the same time?

The safety of our employees is a top priority at DailyPay. With the constant fluctuation of covid cases, DailyPay has decided to extend work from home and opened the office up for the voluntary entrance.

To ensure that we maintain our normal business levels, we incorporated new technologies into our tech stack and emphasized communication throughout the organization. As the cases in New York are slowly dwindling, we’re noticing that more and more employees are coming into the office and going back to a pre-pandemic work style.

What is your opinion on adopting gender egalitarianism from a business leadership outlook?

I founded DailyWomen – the women’s employee resource group at our company – in 2017 because I knew how critical it would be for a FinTech start-up like DailyPay – which is a very male-dominated industry – to prioritize diversity given that our customers are diverse. Something like 60% of our customer base is women, so it is imperative to us that DailyPay aims to attract and retain talented women with diverse thoughts and differentiated experiences.

How I think about adopting gender egalitarianism in the workplace is first illuminating the differences and potential problems we face as a society and organization. DailyPay actively fights against systemic biases and fights for gender equality in the following ways:

  • ERG – DailyWomen programming encourages participation from our allies. We continue to discuss key topics like mentorship, sponsorship, and seeing diverse perspectives.
  • Pay equity – We use tools to help us understand how other people (gender agnostic) are getting paid in similar sizes, industries, and locations.
  • Merit-based rewards – Promotions and reviews are based on a standard set of values and objective performance measures.
  • Goal setting and individual development plans – Every individual at the company goes through the same process of developing a career plan.
  • Blind resume screens – To eliminate the potential for bias in the interview process, we review resumes for performance and merit and nothing else.

Personally, I enjoy spending my time mentoring rising female leaders and have female mentees who may have faced similar challenges as me.

As an established industry leader, what would be your advice to the budding entrepreneurs and enthusiasts aspiring to venture into the financial services industry?

There is so much happening in financial services and a lot of disruption from emerging FinTech companies like ours. Whether it’s new ways to provide access to capital for employees or crypto, our legacy financial system is ripe for innovation, and there’s a lot of novelty in the space right now.

I encourage leaders, enthusiasts, and entrepreneurs to stay curious by consuming, reading, and participating. I recently started using Affirm as I was curious about the user experience and point of sale installment loans. I also love the integration of Venmo’s new crypto wallet. What I love about these companies is that they’re empowering consumers and delivering new value to groups that may not have been able to have access before.

Some of my favorite publications and podcasts that keep me informed are Morning Brew, The Motley Fool, Finimize, Andrew Sorkin’s DealBook, and Planet Money.

How do you envision scaling DailyPay’s services in 2022?

The year 2022 is an exciting year for DailyPay and the Growth team. We have new products and services that will deliver value for companies and their employees. Our scaling plan involves thoughtful go-to-market execution and great collaboration between teams so that we continue to deliver a great customer experience.

Please give us a few testimonials of your clients/customers and a list of awards/recognitions that accurately highlight your organization’s position in the market.

  • IntelyCare, which has about 30,000 nurses on its platform, launched DailyPay’s EWA product in June 2021 through a partnership with Denver-based human resources outsourcing firm ADP. Shortly after, IntelyCare reported a 300% rise in placements over 2020. EWA is not solely responsible for that growth, but it is a perk in a labor market in which the professionals have an unusual mix of financial challenges and burnout but lots of options for where to find employment. –
  • The DailyPay app was a welcome relief for Kroger’s 400,000-plus employees; Monti said: “Overall, the feedback is extremely positive. People see it as insurance. ‘It’s there if I need it; I have the app, I’ve downloaded it, I don’t use it all the time, but I know it’s there if I absolutely need it,’” she said. The app was also a big help recently during the snowstorms in the South. With many workers in Texas having trouble getting their paper checks in the mail during the storms, many workers turned to DailyPay to get paid. –


  • TIME Magazine: The Best Inventions of 2021 Special Mention
  • Newsweek 2021 Top 100 Most Loved Workplaces by Most Loved Workplace
  • HR/WorkForce – Best Innovative or Emerging Tech Solution 2021
  • Global Brand Magazine – Most Trusted Earned Wage Access Provider, 2021, New York
  • 2021 CB Insights Fintech 250 List of Top Fintech Startups