Interview with Kym Insana, President & Founder of Always on Digital

I’m thrilled to have one of my favorite people here – Kym Insana, who won a multi-million dollar RFP competing against 50 agencies. She’s sharing the secrets to her success.

Start With Their Challenges, Not Your Capabilities

Chala: Tell us what you do first.

Kym: We offer advertising solutions helping agencies and brands execute media campaigns across all channels, plus strategy for brands needing extra agency services.

Chala: How did this opportunity come up?

Kym: One of our sales reps was out there sharing our story and learned they were having an agency review looking for a new partner. He said “those are all things we do well and we can help you.” We got put into the RFP process with about 50 total agencies – creative and marketing. The entire process started October-November last year through final decision end of January.

Chala: What did you do differently to win such a huge competitive RFP?

Kym: You and I did a lot of work talking through our story and how we’d approach it. I knew we had all the pieces and were confident in what we could do. However, when you’re only given short time in front of the client reviewing so many different RFP responses, what you say initially – your first impression – matters most. That’s where we were off the mark initially. When I shared our deck, you nicely told me “this is not good, you’ve got to scratch this” because we weren’t hitting their challenges first. It’s a mistake we all make when we want to talk about ourselves and companies we’re proud to represent. But we sometimes forget we’re supposed to focus on the challenge we’re there to solve. When we switched that around and went with that message first, it hit home and really opened everyone’s ears to listen to the rest.

The Phoenix Rising Story Built Instant Trust

Chala: How did you get their attention and trust right away?

Kym: We started with our Phoenix Rising story. It hit home on so many levels. First, their previous partner had let them down by not paying attention to their campaign with human eyes – there was a lot of AI and it’s easy to let AI take care of things, but when you take your hands off the wheel too long, things fall apart and no one was catching those things. That’s one reason we started Always on Digital. The second reason was to create work-life balance for mothers and parents. That also hit home because some folks on their team had been at big agencies where they were told “family time is 5 p.m. to 8 p.m. and everything outside is work – you’re expected back at 8.” They understood happy employees have better performance, they’re more loyal, they make sure everything works. People’s happiness drives outcomes. If you have disgruntled employees, it won’t benefit your business. Those two things really resonated. Then we went into challenges we solved similar to their own – how we’ve helped other advertisers like them solve these problems instead of just spinning up what we do, what we offer, where we run.

Chala: What’s the biggest secret of winning RFPs in terms of figuring out the pain?

Kym: Figuring out their pain can be very simple – ask questions. What is their pain? Can you tell us about relationships in the past – what’s been great and what hasn’t? Where do you feel you want things going? What’s your vision to improve? What are your goals for this year – drive more visitors, more sales? How do you feel you’re going to do that? What do you think you need? Sometimes they don’t always know what they need to get there, but they know they want to get there and maybe you have those ideas to guide them.

Case Studies Matched Exact Pain Points

Chala: I remember forever trying to get you to give them less of the “how,” but you knew exactly how much to give. What other things did you change from past RFPs you lost? How about social proof – how did you bake in proof of success?

Kym: We went strong with case studies – we’ve used them before but we were more aggressive in matching exact things and sharing numbers in a better way. Sometimes it’s hard to get permission to share those numbers and you have to be cautious, but be creative in your story. Sometimes the case study isn’t about increased ROI – maybe it’s they spent two years working with you and haven’t left, they’re an existing client still, or they’ve given testimonials saying you’re the most transparent person they’ve worked with. That shows your ethics and honesty. Using current clients in a way to get new clients makes everybody comfortable – they don’t feel like they’ll be competitive with what you have now. We were pretty clear on those boundaries – one thing won’t cannibalize the other. We had clear delineation and were purposeful when going after a client specifically so they know they’ll get that attention.

Chala: So you got into dialogue with them. Oftentimes once an RFP is issued, you’re not even allowed to talk to them. But you have to have targets in your crosshairs to get in front of decision makers way before that “do not talk to us” period begins and mine them for their biggest pain points, right? Then matched your case studies to their exact pain points they were firing the incumbent for.

Kym: Yes, absolutely. And having the information, sometimes reading between the lines – we spent hours going through this RFP because there were just little things we thought “wow, that seems odd they’d put that in there. What do we think that means?” That’s when you start thinking outside the box – it seems like they’ve been burned. The way they’re talking about certain things feels like somebody took hands off the wheel. So speaking to those things in a truthful way – those are all features or products we have, this is all real life. But sometimes we don’t think of matching those things and we just skew off the elevator pitches or what we think people want to hear. But there could be some little thing your company does or offers that matches so well to their pain point. Just focus on that and not all the other noise.

Bring the Actual Team, Not Just Pitch People

Chala: Did you get a sense of what you did differently or better than all the other RFPs?

Kym: They said we hit on their challenges, but meeting us – a lot of us went in person. We didn’t just bring the pitch people. We brought the everyday folks because sometimes you have somebody that sells you something and you love that salesperson, then they pass your account to someone else and your service level declines. For them being able to see, feel, and touch the actual people that would work day-to-day on their account was important because they needed to feel quality would be the same from the top down. There wasn’t going to be “okay, we’ll give you a junior person who started last week and doesn’t know what’s going on. Sorry, but we already won your account, we’ve got your money, and now we’re moving on.” They needed to feel we’d be committed. Certain things matter to people and you take it for granted thinking “we’re going to do those things anyway,” but it’s important to mention – what are the means of communication, what are the calls like. Sometimes people ask if there are gatekeepers, what’s the process of getting in touch with someone. Those are all indicators they’ve struggled getting in touch with their account people before. Making them feel at ease upfront – we’re going to give you an alias, Slack channel access, you can contact anyone for real. We’ve shown them that throughout the planning process. Having those actual team members during the pitch made a difference because with a service-oriented product, it’s hard until you experience it to know if it’ll work. Seeing the team really made a difference and made us stand out.

Chala: Was the team subject matter experts in their individual roles?

Kym: Yes. Everyone took a turn speaking during the meeting to show their expertise in their area – reporting, day-to-day running campaigns, strategy, account management. Everyone stepped up and showed their passion, which is critical. Not everyone is comfortable in meetings and pitches the same, but when you’re really passionate, even if you’re shy, it comes through. I think that helped sell it honestly.

The Emotional Moment That Signaled Success

Chala: What were some cues you got that it was going to be a go?

Kym: One decision maker came back near the end of the presentation and said “You know what? I’m going to get emotional a little bit about the way you set up this company and what you’re doing for people. It’s just amazing.” I felt like they really did love us as people after. They were so comfortable and kind. We got some hugs. You always feel like you want a high five but never want to jinx it. We did feel like we really stood out. There were follow-up questions and things, but you never know until it’s finalized. They did a really good job picking a creative agency as well and we felt they made a really good match between the way they wanted to do things and the way we wanted to do things.

Don’t Sell Scared – Be Selective

Chala: Last words – what advice do you have to people desperate to land a multi-million dollar RFP like you?

Kym: I always told my sales reps: when you sell scared or desperate, you’re never going to pick the right things. It’s always better to be thoughtful about something and maybe say no and let the right opportunity come to you versus trying to force something that’s not the right fit. Winning something for a short amount of time is a lot more work and a lot less money than winning something for a long period of time. Don’t sell scared. It’s better to find the right opportunity and focus and put your energy on that than looking at a lot of things and trying to just get something in because you’re going to end up picking the wrong thing to bring on.

Chala: I love that. Win rates on RFPs go up like double when the amount of RFPs you’re writing go down. It’s not just math – it’s because you’re being more selective and choosing things where there’s a natural 100% fit between what they’re looking for in terms of their pain and what you specialize in. That’s a marriage made in heaven. You’re not just dry writing, throwing them out there to see what sticks. That’s when it’s all on paper, when you haven’t done the work to meet them offline, haven’t had conversation or dialogue or relationship. That’s when it’s hard to compete against just paper and price, and it’s never about price even in government. When they want you, they will find a way to get you and make sure you’re there for them.

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