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Jennifer Raines-Loring Shares Her Most Effective HR Strategies with Kage Spatz

HR Strategy Series, Real Human Resources

Springboard Retail Human Resources Hiring Strategies

The vast majority of humans will spend the greater part of their lives working. So I’d like to shift the conversation to be far more celebratory about work. I think the change in mental framing may help many people find much more happiness and gratification in their professional, and overall, lives.

As a part of my HR Strategy Series, I’m talking to top experts in the field to teach prospects what hiring managers are actually looking for, while also supporting business leaders in their hiring and retention strategies. Today I had the pleasure of talking with Jennifer Raines-Loring.

Jen Raines-Loring currently services as VP of People at Springboard Retail, the leading POS and retail management software company. Jen is a commercially-oriented human resources executive who combines a strong strategic, operational, and managerial background with a true passion for people and talent functions. Jen pursued a career in HR after a decade of success in direct-to-consumer commerce with companies including Lilly Pulitzer, Swarovski, and Greycork. Jen specializes in developing scalable, efficient people operations, employer brand building, full cycle talent acquisition, remote work, and designing and scaling culture. She holds an MBA from Harvard Business School and a Bachelor’s of Science Degree from the Fashion Institute of Technology. Jen resides in the greater Boston area with her husband and daughter.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I went through a highly formative series of roles coming out of business school, and people issues were clearly the unifying theme. From COO of seed-stage start-up, to managing a 300-person team, to overseeing operations for a company acquired by a large global brand, I got my hands really dirty in a variety of business contexts. The things that drive performance became clear to me — leadership, coaching, performance management, culture, and team building. These functions are needed in every environment, and I found myself more drawn to work on these issues in order to get the real root cause of broader business issues.

In one of those roles, I also had a very bad experience with an established Human Resources team — it felt like HR out of the 1980s, completely focused on legal compliance and risk management but no value add activities that were desperately needed in a company that was undergoing massive change. In that situation, the lack of a competent people function tangibly destroyed value and cost people their jobs. Though difficult at the time, it was the best thing that happened to me because it left me feeling like there must be a better way, and I’m going to do just that.

Can you share the most interesting or funny story that happened to you since you started this career? Can you tell us what lesson you learned from that?

The most interesting thing that has happened to me since “officially” transitioning my career to HR is the sheer number of puzzled expressions and questions I get about why I would possibly want to focus on this area. I get a lot of comments like “but you are an entrepreneur/innovator/leader/etc.” as if these traits are fundamentally incompatible with a career in HR. This was very hard for me at first, especially post Harvard Business School when professional expectations (however self-imposed) seem to sky rocket. I’ve learned that HR, historically, probably really has been in sore need of improvement (in general, not in every case of course). I have had literally no one say, “I had this positively life changing experience with HR so I can totally see why that’s a great career for you!” So I want to be the cause of people saying just that moving forward. There is nothing but opportunity in this field.

Are you working on any exciting new projects at your company? How is this helping people?

I’m working to improve large group virtual communications, such as company meetings. Springboard Retail is a fully distributed team with Springboarders around the country and world. Moments when the company comes together to share and learn are therefore especially critical, and we execute this all completely virtually. I’m exploring collaboration and communication technology in general, as this area is changing rapidly and has the potential to really improve both employee experience and performance.

Large group meetings are some of the most important moments for people to feel that their work is connected to broader goals and develop trust in leadership. I think these moments disproportionately impact overall employee experience for better or worse, so I feel a huge sense of responsibility to get this right for every single Springboarder.

Fantastic. Let’s now jump to the main focus of our series. Hiring can be very time consuming and difficult. Can you share 5 techniques that you use to identify the talent that would be best suited for the job you want to fill? Please share an example for each idea.

Create a recruiting process that has just the right amount of structure. We provide enough structure so candidates perceive the process to be thoughtful and fair. But beyond that, our company values proactivity and self-directed action, so our recruiting process gives candidates many opportunities to exhibit these behaviors. For example, we use a program called Skill Survey that puts the onus on candidates to input and track professional references. Candidates who proactively follow up with references and report back to us in a timely way that their reference checks are complete stand out.

Incorporate relevant technology. We continually seek new tools that not only drive high efficiency, but also reflect our values and proxy our day-to-day experience. For example, we are a video-first company, which means we do EVERYTHING via video. We use various forms of video interviews throughout the recruiting process — one-way, two-way, small groups, etc. We are looking to understand if the candidate is motivated to procure the right hardware and software to effectively connect via video, and is either comfortable interacting via video, or sees this as a fun challenge if they don’t use video in their current workplace.

Allow candidates to speak in their own voice. One-way video interviews in particular (in our case, powered by Spark Hire), have been game changing at the top of the funnel. We ask a series of questions, candidates record responses, and our team can listen to the responses as it is convenient. Given that total time invested is as low as 7–8 minutes per candidate and our team can share the workload of reviewing responses, we are able to move one-third to one-half of all applicants to this stage — this is substantially higher than the rate of applicants being moved forward when we went straight to phone screen. We don’t have to limit candidates to those with ideal keyword matches on their resumes or perfectly aligned experience. Our goal is to give a maximum number of people the opportunity to stand out, even if their background isn’t a perfect match for the job.

Make the right promises so that your candidate experience doesn’t suffer, and then follow through. As you increase automation and reliance on tools in the recruiting process, it’s imperative to manage candidate experience. For example, we promise to watch every single one-way video interview and personally follow up with the candidate. And we do. Every time. We NEVER want candidates to avoid investing 20–30 minutes to set up and record a video interview for fear that it’s being sent out into the ether where no one will care.

Share your recruiting process, end-to-end, publicly. This tactic is easy to execute but easy to miss. We have found that candidates really appreciate a full understanding, in advance, of the recruiting process, so we put it on our website.

With so much noise and competition out there, what are the top 3 ways to attract and engage the best talent in an industry when they haven’t already reached out to you?

Share honest thought leadership — in our case, true stories about what’s happening at Springboard Retail and what we are learning. We skip the touched-up photos and polished taglines about how people love working at our company. Instead, we share about our ongoing attempts to make our company better. We share things that our employees are interested in sharing with their friends (like our journey to becoming a distributed team), which creates a more personalized way to get to know the company for potential candidates.

Related, share the ups AND the downs with the world. Articles like “Where We Messed Up in our Transition to Work From Anywhere” have gotten some of our highest engagement and candidates continually reference this content in interviews. Reasonable people don’t expect companies to operate flawlessly or for management to make perfect decisions, but they do like to know that a company aggressively learns and reacts quickly. Demonstrating that our company is low on ego and high on actionable learning has allowed us to engage with potential candidates in conversational, human way.

Know your value proposition. We feel that people join companies of our size and stage for the dynamism, opportunity, and mobility, so we talk about this publicly. For example, I share aspects of my own path to become VP of People despite a non-traditional HR background. People like to know that the company is willing to help identify and maximize their skills, regardless of what their resume currently says.

What are the 3 most effective strategies used to retain employees?

Workplace flexibility, embodied by our Work From Anywhere policy, has been by far our biggest retention tool. Our retention hovers in the high 90s. Our remote model impacts employee experience on every level, so we constantly seek to innovate and improve in communication, collaboration, transparency, and community-building across our distributed team.

Measure internal advancement. In my experience, this is easy to miss. We rank internal advancement with other top people metrics that we consistently measure, like new hire acquisition cost and revenue per employee. While we are still figuring out what the right targets should be for this metric, we share the figures with employees and we keep a logical mindset. For example, if we were to discover that it’s taking people, on average 3 years to advance, this probably isn’t sustainable.

Create ample opportunity for people to connect with each other. We believe that relationships with coworkers are one of the main reasons people keep, or quit, jobs. Therefore, we take our community seriously and maintain high participation in a range of activities designed to continually deepen professional and personal relationships across the company.

In your experience, is it important for HR to keep up with the latest trends? Can you give some examples of what this looks like?

1000% percent. Our goal at Springboard Retail is to operate HR in a lean, decentralized, high value-add way that is deeply embedded in the business. Historically, it’s been hard to simultaneously solve for all these variables. But where tradeoffs have existed before, technology enables us to innovate and develop ultimately better solutions. So it’s imperative to continually understand new tools, processes, and ways of thinking. At Springboard Retail, we have focused on recruiting first. Because of our recruiting tech stack and approach, we effectively handle thousands of candidates from around the world simultaneously without a dedicated recruiter. Springboarders at all levels support recruiting (which people love in many cases), acquisition costs are low, and our response rates to candidates are high.

Can you give an example of a creative way to increase the value provided to employees without breaking the bank?

Virtual special interest chats. Though this naturally fits our distributed team model, I would recommend virtual community-building activities for even non-distributed teams because attendance is high and costs are low. Particularly interesting sessions for us have been when Springboarders have led a talk on areas of passion, such as cricket, musical theatre, or vinyl record collecting. We typically cover two topics in a 45-minute session, so that people can fully be back in the groove of their work after an hour. There is no friction such as travel time that deters people from attending social events, and the activity is less than an hour, so we can vary the time of day to accommodate different time zones, family situations, etc.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Tough question! Though still a forming notion, I reflect a lot on what an exceptionally positive experience work can be, and beyond financially. I feel that, in general, the discourse on work errs toward minimizing the downsides of this necessary evil. But I feel that if I removed all of my professional experiences, my life would be exponentially less rich, interesting, and meaningful. And the vast majority of humans will spend the greater part of their lives working. So I’d like to shift the conversation to be far more celebratory about work. I think the change in mental framing may help many people find much more happiness and gratification in their professional, and overall, lives.

That new way of thinking can potentially help a lot of people source more happiness at work! Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.” — Steve Jobs

I have stuck it out in tough times in some seemingly random, disconnected experiences, and this quote has been helpful in the low moments. The path from fashion school to head of people at a tech company actually makes a lot of sense to me…in retrospect. Along the way, I have continually told myself that if I give my all every day and keep aggressively learning, it will add up to greatness somehow.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world whom you would love to have a private lunch with, and why?

Doris Kearns Goodwin. She continually inspires me with timeless writings such as, “Greatness and impact are very human processes, influenced greatly by our choices.” In her books, I will read about Theodore Roosevelt, for example, and yet the problems he faces will seem so accessible and familiar. Reading her works reminds me that leadership is an awesome responsibility and I’m really lucky to have it. Given her lifelong study of legendary leaders throughout history, I would be really interested in her perspective on how an HR leader in today’s world could be most impactful.

Thank you so much for these fantastic insights!

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