Kelsey Peterson Of Crosschq: 5 Things a Business Should Do to Create a Wow! Customer Experience

An Interview With Orlando Zayas

Orlando Zayas, CEO of Katapult
Authority Magazine
8 min readDec 23, 2021


Show some love to your customer-facing teams. Though this post is about the customer, we know it is difficult to pour from an empty cup. Your CS teams must be well-supported cross-functionally and their value recognized within your organization. This can come in many forms, such as public praise, financial reward, and personal development resource allocation.

As part of our series about the five things a business should do to create a Wow! customer experience, I had the pleasure of interviewing Kelsey Peterson.

Kelsey leads Customer Success at Crosschq. the HR technology leader that is reinventing hiring to help organizations build winning, diverse teams. Kelsey is an adjunct professor, keynote speaker, and brings an extensive SaaS consulting background to her current role as Head of Customer Success.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Of course. I like to believe I’ve had the customer gene since childhood, as I started bussing tables at 12 years old. The best part of any shift were the people — connecting with patrons, checking on their experience and seeing what I could do to make it better. Fast-forward a decade and I was project managing website builds, ensuring the client delivery met expectations and was on time plus within budget. In the decade since, I’ve enjoyed consulting, working as a CSM, and exploring Strategic Partnerships within the BD world. I’m now managing our CS org at Crosschq.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

Early in my career, the websites I project managed were built using the waterfall methodology. In short order, we shifted to agile development, and — while I had just nailed down design and development acronyms with the former approach — I was now inundated with sprints, scrums, and other terms with which I was unfamiliar. After a couple of mishaps (as it turned out, sprint did not simply mean ‘go quickly’), I learned the value of a quick Google search. Though we had been told in school ‘there is no such thing as a bad question’, a bit of research can often spare you from an awkward moment!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Three people stand out in this regard, each offering an invaluable lesson, as they lead by example through and through.

Kendy Hess was a professor of mine at Holy Cross; her classes fueled my love of philosophy (which ultimately became my major). She taught me to be curious and critical — to ask meaningful questions, challenge assumptions, and be radically open to new ideas.

Dave Armlin was the Director at HubSpot while I was in our CS org. His steadiness was second to none. What I thought may be an escalation was, in fact, an opportunity when surfaced to Dave. He taught me to keep a level head and approach situations with a reassured calmness.

Eva Klein was the VP of CS at HubSpot. She was unrelenting in her principles and one of the most altruistic leaders I’ve had the opportunity to work with. She taught me the value of staying focused on your goals and how to effectively look out for your team with collaboration and candor.

Thank you for that. Let’s now pivot to the main focus of our interview. This might be intuitive, but I think it’s helpful to specifically articulate it. In your words, can you share a few reasons why great customer service and a great customer experience is essential for success in business?

I’m anchored by Jeff Bezos’ assertion that “Customers are always beautifully, wonderfully dissatisfied. Even when they don’t yet know it, customers want something better, and your desire to delight customers will drive you to invent on their behalf.”

I’m of the opinion that working closely with customers to identify their expectations, then committing to doing even better is the only option in a competitive market.

We have all had times either in a store, or online, when we’ve had a very poor experience as a customer or user. If the importance of a good customer experience is so intuitive, and apparent, where is the disconnect? How is it that so many companies do not make this a priority?

Couldn’t agree more here. I think the disconnect comes from a short-sighted or antiquated approach. An early or mid-stage company may think their core priority is net new ARR, neglecting the leaky bucket impact of churn.

Another factor here can be a lack of internal alignment among ownership of the customer experience; it cannot be shouldered by one team alone. All teams (regardless of whether they are customer-facing or otherwise) should put the customer experience first, followed by what is best for the organization.

Do you think that more competition helps force companies to improve the customer experience they offer? Are there other external pressures that can force a company to improve the customer experience?

Absolutely. More competition helps companies recognize they need a leading product and customer experience to stand out.

Compelling loyalty among a competitor’s customer base should illuminate an opportunity for your organization to improve its customer experience so you too have your growing community of evangelists. These advocates can help you through the entire customer lifecycle — from marketing (offering a testimonial) to selling (joining a call to speak to a prospect) to renewing and upsell potential, this is an important cohort for any organization.

Can you share with us a story from your experience about a customer who was “Wowed” by the experience you provided?

There are a lot of them! Our team has a goal of facilitating a customer delight moment each week. Whether we send a Starbucks gift card and make a donation in their name to Girls Who Code (this was sent out just yesterday!) or deliver flowers because the customer reports their Friday is ‘feeling like a Monday’, constantly prioritizing delight is core within our values.

Did that Wow! experience have any long term ripple effects? Can you share the story?

I have customers that I delighted as a CSM five years ago whom I’m still in touch with (though we’re both at different companies now). I’m still on the list to receive one customer’s annual Christmas card of her adorable (and growing!) family. Though the magnitude of the delight moment may not have been momentous, the warmth of the interaction can carry through time. As Maya Angelou shared, “people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

Ok, here is the main question of our discussion. Based on your experience and success, what are the five most important things a business leader should know in order to create a Wow! Customer Experience. Please share a story or an example for each.

1. Delight starts pre-sale. It may sound simple, but ensuring your marketing and sales team are adequately enabled with resources to position your product accurately (and specifically, as needed) is the first step to delight! Customer friction inevitably occurs when a customer isn’t clear on what they purchased, or, worse still, is expecting functionality that doesn’t (yet) exist.

2. A Wow! Customer Experience necessitates disruption. There is likely a particular pain point within your industry that is known, and not yet addressed. Blockbuster didn’t worry about their lack of on-demand content because their competitors neglected this area as well — Blockbuster hit the snooze button and ultimately woke up to Netflix. It’s important to think critically about where your organization may fall short (even if there aren’t others doing it better currently, because there will be).

3. Delight in surprise moments. Nobody will turn down some holiday goodies, but your customer-facing teams should be on the lookout for unique inflection points (such as someone is moving or even just having ‘a day’). These teams should have allocated budget to facilitate a memorable delight moment for such occasions.

4. Meet your customer where they are, as customers are not one size fits all. Particularly in the SaaS space, it’s imperative to understand the specific customer’s goals and priorities (why did they purchase, what does ROI look like for them), as opposed to driving how success is defined on their behalf. They’ll likely look to you as leaders in the space to offer consultation, which is hugely meaningful, but these conversations should be born out of the customer’s goals.

5. Show some love to your customer-facing teams. Though this post is about the customer, we know it is difficult to pour from an empty cup. Your CS teams must be well-supported cross-functionally and their value recognized within your organization. This can come in many forms, such as public praise, financial reward, and personal development resource allocation.

Are there a few things that can be done so that when a customer or client has a Wow! experience, they inspire others to reach out to you as well?

Definitely — CSMs are in large part responsible for facilitating happy customers so these folks are naturally inclined to advocate for the product. Marketing teams are wise to take this to the next level with communities, content, and webinars to help bolster this evangelism.

My particular expertise is in retail, so I’d like to ask a question about that. Amazon is going to exert pressure on all of retail for the foreseeable future. New Direct-To-Consumer companies based in China are emerging that offer prices that are much cheaper than US and European brands. What would you advise retail companies and eCommerce companies, for them to be successful in the face of such strong competition?

Not everyone is your customer, and I feel strongly in the power of an Ideal Customer Profile. It is inevitably the case that Direct-To-Consumer companies undercut US/European brands on price. But will these emerging companies offer better quality? Efficient delivery? A helpful support team for questions or returns?

Some consumers may opt for a less expensive option, and that’s okay. However, many of these consumers will return if they find the lesser-priced option has downsides they did not anticipate. As such, I’d recommend retail companies and eComm organizations prioritize the customer experience. Marketing teams can set up powerful customer marketing drip campaigns as well to delight customers into returning (such as birthday discounts).

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Ah… utilitarianism! My priority right now is helping companies hire and retain better — this includes fair chance hiring, reducing bias in the hiring process, and ensuring folks are set up for success when they onboard. I’m grateful DEI is a priority right now for many organizations, but the belonging aspect sometimes is neglected. As I’ve heard it said, ‘it’s one thing to be invited to the dance, it’s another to be asked to dance’. Hiring diversely is powerful — we must look to the next step to ensure these new hires are empowered to see success in their new roles.

How can our readers follow you on social media?

LinkedIn is your best bet:

This was very inspiring. Thank you so much for joining us!

Grateful to be here — thank you, Orlando!