Founder @LegUpHealth, VP of Revenue Operations @WindfallData, Podcast @StartuptoLast, Writer @ https://xitter.cf/t.co/y53wcEV9Mf

Utah, United States
Joined May 2011
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So proud to be a small part of this!
🔥 Beyond excited to announce our $65 million investment from Morgan Stanley! 🔥 I'm so proud of the entire @WindfallData team and the growth that @DRS85 and I have seen over the past several years. We're thankful to our 1,500+ customers. It's been an amazing journey thus far and we can't wait for the next chapter. Let's go!!! windfall.com/company/news/wi…
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Rick Lindquist retweeted
One of the biggest questions we’re hearing from clients right now is: "How do I keep offering competitive benefits when I also need to cut costs?" It’s a valid question, especially when benefits are often the second-highest expense on the books—right behind payroll. leguphealth.com/blog/navigat…
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First personal newsletter send of 2025. Hoping to write more this year! ricklindquist.kit.com/posts/…
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Replying to @Appfire
@Appfire I'm having a horrendous experience with your customer support team troubleshooting your Confluence / Salesforce integration. Can you please escalate me to someone who can help? I've been working through this for multiple months at this point with no resolution
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Replying to @mattjlayman
Yup - that’s my situation as well. Trialing the app now. Hard to justify paying (more) to watch when the team isn’t that great.
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Replying to @mattjlayman
Did you figure this out?
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Rick Lindquist retweeted
Live in Utah? We'll help you find, use, and manage your health insurance

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Have been an executive (VP level) at a high growth startup for 3 years or so. And I can assure you that it is no where near as hard as being the full-time CEO of a startup, high growth or not.
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Yes - Tyler hit the key point. Over 100 employees health insurance rating rules for small employers change so that would be the break point for the “small business health insurance offering” - one thing we will need to decide is whether we want to continue to service those - I think we will want to as our “job to be done” doesn’t change much.
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Replying to @aarondfrancis
I got so confused on book 1 lol - need to revisit
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I'm curious because I think we need to do more middle-funnel offer experimentation with @LegUpHealth and it's something we have not done before
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Replying to @CasJam
When you say landing page for something new, does that refer to an offer related to a service you have up and running? Or is it more a of a new idea entirely?
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I'm using generative AI daily now and I just keep finding more ways to use it. Pretty neat.
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Replying to @willking
Haha - I can't wait to hear how TK does with the mac
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I'm super grateful to work with @jdcleary and @TylerMKing on @LegUpHealth. Our monthly partner meetings are awesome and productive. It's a side project for me, so I typically don't get to spend a ton of time with both of them at the same time. JD is leading the way with daily execution, and Tyler brings a long-term perspective w.r.t. to decision-making that we couldn't replicate without him.
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Replying to @CharlieYalf
Loved both of them! Agree with the similarities too - and really enjoying the live action versions they are doing right now.
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It is so hard to tell the difference here. I can relate to the OKR/Google example. Wouldn't it be nice if implementing a goal framework automatically made your company or team better?
A company can succeed 𝘥𝘦𝘴𝘱𝘪𝘵𝘦 its processes, not 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 of them. How do you know which is which, in some organization you’re wanting to copy (e.g. Google’s OKRs)?
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Just wait til you have a kid and you get automagically added to the pediatrician email + txt list :)
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