How Jennifer Henderson Had 60 Pitches in 90 Days and Raised $30M

Key Takeaways

• Jen's journey began with a personal experience that fueled her passion for improving parental leave.
• She faced significant challenges as a first-time female founder, including fundraising hurdles.
• Navigating the COVID-19 pandemic provided unexpected growth opportunities for Tilt.
• She advises female founders to focus on success to pave the way for others.
• AI's role in HR tech is complex, with buyers being cautious about AI-driven solutions.

Jason Kirby:

in case anything comes up. the main purpose of our team will cut this all up and get it all dialed in for us. But we'll record for pretty much the full hour. We'll try to stop at the end of the hour in case you have something coming up. And then are there any questions for me before we get started?

Jen Henderson:

Ready to go.

Jason Kirby:

And you guys, I think you reached out originally following our newsletter, correct? How'd you find out about our newsletter?

Jen Henderson:

Yep.

Jen Henderson:

I subscribed years ago. I couldn't even tell you where I originally found it. Yeah, it would be interesting to actually look at the subscription date. I'm sure you have that in your CRM probably. Yeah, let's do it. Where did I find Jason Kirby?

Jason Kirby:

Yeah, actually, yeah, let's take a look at that. That sounds fun.

Jason Kirby:

So that's me the... here we go.

And was it, guess where we always subscribe from your tilt email? Yeah, that's okay.

Jen Henderson:

No, we used to be career allies. was our first file. Actually, it's still our legal structure,

Jason Kirby:

So looks like you subscribed March, 2024.

Jen Henderson:

Yeah.

Jason Kirby:

Is that something about right or are you following before then?

Jen Henderson:

I was probably following before them, but like I said, I was under Career Allies, Inc. But I, yeah, it would probably be helpful, right? If I knew where I found you, you'd like to meet me.

Jason Kirby:

I got Korea, ABBA, Ally, DBA, Tilt. Let's see.

Jen Henderson:

Yep. That's us.

Jason Kirby:

I know came up, it's still the same email. So one contact. if I can find it. yeah, it looks like maybe you reached out to one of our partners, Interplay Adventures. And I think that's how we got originally connected.

Jen Henderson:

Okay.

Jen Henderson:

What was the name of the venture fund?

Jason Kirby:

Interplay Adventures.

Jen Henderson:

let's see.

Jason Kirby:

So we, they're investors in us and we work very closely with them. came out of their boundary.

Jen Henderson:

Yes.

Yeah, Caroline, where are my contacts there? Caroline and Mark.

Jason Kirby:

What was that? yeah, Caroline, yeah. And then can you share who you raised money from?

Jen Henderson:

yeah, all of them. Our cap table is actually, I would say, pretty small. And they're not well known. So I've never looked to raise from our, you know, the blue chip funds. The fund that led our series B is named Bramalee out of Boston, very small, spun out of fidelity. Our series A, Origin.

Jason Kirby:

off of all the above.

Jen Henderson:

our A plus firework, which has now stopped. The fund has moved on. And before that was all seeded in angels.

Jason Kirby:

So let's talk about that. So let's go ahead and break into character here and I'll lay things off. We'll talk about the B round and I also kind of caught the story because I heard you on another podcast say where you're the, checked all the impossible boxes. First time solo female founder with kids raising money. Yeah, that's kind of the odds were stacked against you, but yet you pulled it off. So I think it'll be a fun conversation.

Jen Henderson:

Okay.

Jen Henderson:

Yeah.

Jason Kirby:

All right, so I'm going to go ahead and kick things off, welcome people back to the show, and then we'll dive in with the first question.

Hey everyone, welcome back to Fundraising Demystified. Today we have Jen Henderson with us on the show, founder of Tilt and quite the successful founder of raising over 30 million post Series B in the HR tech space. Welcome to the show, Jen. So I just want to go straight in. We were talking offline for a moment here about your capital raising and how you chose not to raise from your typical tier one.

Jen Henderson:

Thanks for having me.

Jason Kirby:

investors and how you have a small cap table but maybe a lesser known cap table. Let's talk a little bit about your fundraising journey and how you ultimately navigate it to get to the point where you closed a Series B not too long ago.

Jen Henderson:

all the way back in the day, right? To the post idea stage, but what am I going to do with this idea? I remember sitting at a table with a advisor saying, well, are you going to bootstrap this or are you going to take on venture? And I will be honest in saying, I didn't even know what the difference was. So the decision to pursue venture came from a very naive positioning of, see a real problem and I want to solve it. What does that mean?

Jason Kirby:

Thank

Jen Henderson:

And that means I need to take on capital and I need to scale through technology. So I would say it was almost a known path forward because of the North Star of wanting to help as many people as fast as possible. And anytime you say as fast as possible in my experience, you probably need to take on capital. And I don't come from money. I don't have rich relatives. I wasn't willing to second mortgage my house. I wasn't willing to drain my family's financial security. So

that leaves Take On Venture. And so that started our very first round in 2019.

Jason Kirby:

And so, coming from that position and starting your first round, coming to that conclusion that grow fast, don't put up your own capital. Where would you kind of get started? So you're kind of relatively new to this landscape. How did you educate yourself on what was the appropriate type of round and how much to raise and where to go?

Jen Henderson:

Well, I think the nice thing about being based in the middle of the country, I say in Colorado is options were pretty limited in terms of where I could pursue taking on that first capital. Again, being a first time founder with young kids, I wasn't willing to go live on the coasts and walk up and down and knock on doors. So I had to be more resourceful. And for that.

Colorado has actually the oldest angel network in the country that's called Rocky's Venture Club. Rocky's Venture Club is comprised of just really awesome humans who put on free education, who lead workshops, and who were accessible and available to me to advise me as to how to even go about starting this thing. So I mean, all the way back to what should I put in a pitch deck?

And like what competitions do I apply to? There was a point in time where I pitched 60 times in 90 days. Every possible stage I could get on, got on. It was truly you press a button and my pitch came out. Um, was great learning environment for me. And it was a great opportunity for me to get our story dialed in. Um, and ultimately resulted in our first 190,000, I want to say. Um, but that took all of six months and a lot of pushing the boulders up the hill.

And we got a torque.

Jason Kirby:

And that was in 2019, kind of the first round. And then one thing to go out and sell your story, meet some great people that back you, but what were you building? What was kind of the initial concept of the product that ultimately attracted that?

Jen Henderson:

Tilt was born out of personal experience. So I had two really shitty leave experiences in corporate America. And the second so egregious that it was the straw that broke the camel's back. I wanted to make leave better for others that were like me. And unfortunately, leave gone wrong is a very common pervasive problem. So I wasn't unique. There was nothing special about my situation. But we came out of the box.

focusing on parental leave because that was my lived experience was having a baby and having it not well supported. I learned very, very quickly that that is one flavor of leave. And I had a really kind CHRO say to me, you can't leave all my other leaves held together by duct tape and band-aids and only fix parental. So that was all I needed to hear to say, all right, well, let's expand this. And so very, very early on, we expanded our services to supporting all types of leave.

in all States in the union. and that was the product that we came out of the box selling in late 2019. When I say product, it's kind of, you know, what do they say? If you're not embarrassed by your first version, you probably waited too long. didn't wait too long. There's definitely, some, wow, I can't believe that's what we started with moments, but we did. And I took the really bad advice. I would say in hindsight that if you're not your company's first salesperson, you should never expect anyone else to sell your product.

I now believe that there is such an expertise in art and craft to salesmanship that expecting anyone to do that regardless of their backstory is flat advice, I would say, and irresponsible in my case. Whatever, I did it. I took the advice. I was my company's first salesperson, got the first couple of contracts across the finish line. And just for the record for your listeners, they weren't like...

my network, I didn't call people and say, do me a solid and sign this contract so that I can show early traction. This was absolutely like hit the pavement, cold selling, trying to figure out how to sell you, you name it. was throwing shit against the wall. but that first product did get us our first, couple of contracts and then COVID happened. And quite literally we were in a war room in March, 2020, trying to figure out how to support our small but mighty customer base.

Jen Henderson:

navigating COVID-19 related leaves. And that very quickly spun our velocity. It's the tailwinds founders dream of, I've said before, and I mean it. I don't know where we would be if we didn't have the pandemic come to the world in the day and time that it did, honestly, with the work that we do.

Jason Kirby:

So you kind of, you had the product in place and enough contracts in place to be able to have the foundation to really scale during the, COVID. So you have this experience, like what are some of the numbers or KPIs behind the growth from your seed to your series A and like, how did you think about the next capital round?

Jen Henderson:

Yep.

Jen Henderson:

Well, I had everything said to me from as soon as somebody pays you a dollar for your service, you've made it to unless you hit your first million, you've made it and anything in between. So there were a lot of opinions and my younger self, if I could go back and tell her anything, it would be stop listening to everyone because being a first time female founder, I thought, well, I don't know what I don't know. So I'm going to, I'm going to listen to all of this advice. So I say that under the cover of careful who you take advice from in the early days.

but our KPIs at the, you know, back of the napkin to, would say the first half a million, were predominantly traction. Who are we selling to? How big are the contract sizes? How long is it taking us to sell those contracts? We sell annual contracts. So for us, once we sold the annual, we had a whole year to ensure that we're getting that renewal because now eight years in, as you might imagine, the KPI scorecard has changed quite a bit, but.

In those early days, was velocity. was, you getting people to buy the product? Are you solving a real problem? You'll hear, is this a vitamin or a painkiller? So all KPIs are pointed to proving this was a painkiller and not a nice to have or a vitamin. And in hindsight, it was kind of as simple as that. was get sales. Get sales as fast as you can and then get as much as you can of them.

Jason Kirby:

What was your magic trick to get sales? Like what were you guys doing? What was the, was it still you at that point? Were you bringing on help to scale that effort?

Jen Henderson:

No, it was not me. The answer, which is unfair to your listeners, is my vice president of sales found me and she was my third hire. And she was and is my magic ingredient. She's absolutely phenomenal. What she has created then and now in this organization from not only the go-to-market infrastructure, but the continual iteration and the continual growth has been.

Honestly, a thing of dreams. I, my board members are continually just flabbergasted at her ability to continue to grow and scale. So the only replicated bullet advice I can say as to what we did in those early stages is find an excellent go-to-market leader way easier said than done. And I completely acknowledge that.

Jason Kirby:

You had to build something and be someone that was worthy of attracting that kind of talent. So you had to do something right at that point. And when it comes to the capital raise, so kind of walk us through, you're now starting to get this breakout velocity, you're starting to work with the team. Kind of walk us through the series A.

Jen Henderson:

Thank you.

Jen Henderson:

Yeah. We went through Techstars. So I made the decision pretty early on. Again, I don't know what I don't know. And that came from a place of if we're going to do this and be successful. I had three hypotheses that I needed vetted in choosing an accelerator. One is I want the street cred. I want the badging to mean something in the market when I go for subsequent fundraisers.

Techstars and Y Combinator at the time were the two that seemed to get the most legitimacy behind it. Two, I wanted a vetted curriculum. Like I said, I wanted somebody that was gonna teach me what I don't know about term sheets, what I don't know about scaling, et cetera, et cetera. That again, checked out with Techstars and a couple others that I was considering. And third, I said it before and I'll keep saying it, I'm a mom with young kids. I was not gonna go live on a coast for three months and lock myself in a room.

and sit around with bunch of people in hoodies. Like, it's just like, no, that's not the stage of my life. And it was not interesting to me. Believe it or not, probably not surprising to you, that criteria whittled the list down really fast. And we were actually accepted to two accelerators at the same time, ultimately picked tech stars, primarily because I had more compelling reverse diligence individuals who were like, yeah,

get a great MD first and foremost, but worth it. second, the MD of our class in particular, it was a very fast, I get it. Like he knew the problem we were solving. There was no double cell in my experience. It was like, wait, why is leave broken? I just immediately know I'm talking to the wrong person. What is that type of a posture? So we did, we took...

We took the Techstars Accelerator, the very first workforce development cohort that Techstars has ever stood up. And that really propelled the Series A. And we were preempted in our Series A upon graduating from Techstars. We worked with that lead to fill out the round and we were off to the races. And I say that somewhat tongue in cheek because no part of our fundraising journey has been easy, but that was.

Jen Henderson:

That was probably the best round, I would say, from an ease of process sampling.

Jason Kirby:

And what was your, what, was the timing? What year was it? And what was the traction you were at at that point?

Jen Henderson:

2020, about a million.

Jason Kirby:

Okay, so that was kind of the benchmark back then in 2020 and it was pretty hot for investors to kind of come in, especially for things that were catching the tail lens of COVID. And then how much did you raise in that round?

Jen Henderson:

Ooh, that's a really good question. I want to say five plus or minus is what's coming to mind.

Jason Kirby:

So.

Jason Kirby:

So decent round coming out of, especially coming out of Techstars. Usually Techstars a little bit earlier, most people are coming out of Techstars pursuing their seed. So it sounds like you had a good amount of traction and going in and then coming out pretty quickly. Yeah, no, it sounds like based on what you were sharing, it sounds like we're, I would say later stage than what Techstars would typically come into contact with.

Jen Henderson:

Yeah, we were the farthest along in our class, for sure, by far.

Jen Henderson:

Yeah. sorry. I'm just going to say on that point though, I tend to be pretty contrarian in general and that typical like stage and size of, of tech stars. just, I don't know if it's welcome advice or not, but I kind of throw that out the window. Like if, if you need it, regardless of your ARR, go get it and convince them that it's worth it. It was expensive capital. We mean that far along, you know, tech stars doesn't do what they do for free, but.

Jason Kirby:

You know, at this.

Jen Henderson:

paid off in spades. Every rod we've had since Techstars, there's been a Techstars connected tissue somewhere somehow.

Jason Kirby:

That's a super powerful testimonial to them and I work very closely with Techstar so I know them quite well. I think also you've acknowledged and you mentioned it many times, you don't know what you don't know. I think for the audience to give them a step back, you were in the corporate world prior to that but even before that, you started as think a

a Starbucks store manager, and then they kind of scaled your career all the way to this point of running a Series B VC-backed That's a pretty extensive career learning path. I guess give the audience just a little bit of color of what that career trajectory was. And I know you had the pain point to legit solve this problem, but kind of choosing the path of startup as opposed to corporate life.

Jen Henderson:

I started as a barista and it's, yeah. It's a weird circuitous career path for sure. And I never pursued startup or entrepreneurial ventures in any way, or form. I loved corporate America. It provided so many opportunities and access to so many intelligent people.

Jason Kirby:

wow, even... okay.

Jen Henderson:

I was really proud to work for the Starbucks organization for the years that I did. In hindsight, I have tapped into that learning journey more times than I can count. It was truly for a formative professional career like Learning Ground, phenomenal. The only reason in all transparency that I pursued startups is I was really pissed off. I was really, really mad.

And if I wanted to effectuate change, was either, you know, get, get gobbled up into a corporate America and do more of an intrapreneurship, which that was an option. I could effectuate change, but albeit like constrained change. And that just wasn't interesting to me. If I was going to go for it, let's go for it. and yeah, I had a really supportive and still have a really supportive husband. He's like, we can live off one salary, firefighter salary. like, let's be real. It was clipping coupons. yeah.

Jason Kirby:

Yeah, live and lean.

Jen Henderson:

for a while and that's what we did. So it was in no way, or form architected. had no long-term vision for this. I just was, I was really mad. And I will say in hindsight, that connected tissue to the pain and looking my kids in the eye every day and having the reminder, if I don't make this better for them, they could very well experience what I experienced is a hell of a fuel to go through the ups and the downs of being an entrepreneur.

because they are significant downs.

Jason Kirby:

Yeah, it's pretty wild ride. You get the high, but then the low comes real fast right after that.

Jen Henderson:

Whoa. Yes. Yeah, you got to hold on that high as long as you can.

Jason Kirby:

So.

and then convince everyone that you're going to stay on that high as long as possible before that low hits so that you can get the capital, get the deals, get the talent, and then try to assume the entire burden of the low to yourself. So no one has to, no one else has the deal. It's the of this founder dilemma of carrying the burden. So when it came to subsequent rounds, because like you raised a little bit money and then you did the series A, but you've gone on to raise well over 30 at this point.

Jen Henderson:

Thanks.

Jen Henderson:

That's right.

Jen Henderson:

Yep.

Jason Kirby:

And you mentioned there's no easy journey. What were some of the tactics that you used in leverage in your subsequent rounds?

Jen Henderson:

Every round felt like a new round. And I lead with that as unfortunate news. I think I operated with the hypothesis of like, you go to the gym every day and it gets easier and easier. This, you know, every time should get a little easier. That was not my experience. I also operated with the hypothesis that we have proven more and more product market fit with every iterative round, because we've got more ARR, we've got more replicatable, you know, behind the scenes machine and our GTM, et cetera.

The truth of it is, is the rounds in the macro economy played significant roles as to how

hard, easy, I can't say easy. I can't in my good faith ever say around was easy, but unique, I guess, headwinds or macro determinate. And the reason that I say they were all different is, man, as a female founder, the finish line is not only constantly moving, but sometimes not even present, like evaporated. So where I would look to playbooks as, all right,

I know I need these top quartile numbers. know that founders that I've talked to and investors say, you you need this, whatever, NRR number or year over year or gross margin, you name it. Like give me a, give me a goal and I'll crush it, but don't give me a goal and then move it on me. And that was what I experienced pretty much every time to different degrees of severity in these rounds. So after I got done ramming my head into the wall with

those early rounds of like, is like, la la land. I thought, okay, well, control what I can control. Let's get quicker and faster to disqualify funds that are either pulling that BS of moving the finish line or are misaligned with what we've been orienting our business to be successful around so that I can save my brain damage. And two, let's not only get to the top quartile, let's fucking crush it, right?

Jen Henderson:

Let's pick a couple of KPIs that we are going to be next level at and really orient our point of view and our talk track in that process around those. So in the series A2, think, I always think the semantics of rounds are hilarious. This one led by an awesome firm called Origin Ventures, who's some of my favorite humans out there. You know, we went in with a really tight, here's our year over year growth.

Here's our engine, our GTM engine dynamics that we can prove. You pour this in, you get this out. And at that time, I think our third lever that we were really orienting around was probably the automation at that point of the maturity of the company. So we we, we tighten the story. And I would say dissimilar to that in the series B, it's all about the numbers. So my story became very much secondary.

And the diligence was in every financial report and otherwise that you can imagine, which is just a different ballgame.

Jason Kirby:

So what was your process to get to origin?

Jen Henderson:

Origin was Techstars. Techstars' introduction, they found us. What I loved about that story is they watched us and we maintained check-ins for probably six months, a year, upon graduation. And I mentioned I'm in Colorado. I'm about an hour and a bit from our airport and one of the partners drove up here to see me and meet with me.

have a conversation over coffee and intentionally like talk about the business. That meant something to me. Now that's not the only reason obviously that we went with Origin, but that personal investment in the relationship of founder investor meant a lot.

Jason Kirby:

As far as bringing other investors going out, so Origins, found you through Techstars and been watching and observing. Did you run a process? Did you wait for them to come to you? Did you go out and pitch 50 investors, 100 investors, three investors? What was the process like?

Jen Henderson:

Every single round, five rounds in so I can feel pretty confident about this data. 100 nos for every one yes. Every single round without question.

Jason Kirby:

Okay, you left that big backdrop. You're just like, they came to us. You also did a lot of work, it sounds like.

Jen Henderson:

Well, 100%. So they come to us is, I think, right that tip of the iceberg of people not knowing all the work underneath it is 100 no's to everyone, yes. Also, what's interesting about the Origin Round is I had another term sheet issued at the same time. And what was interesting about that is I told that investor, as I've told every investor, I need the most plain-jane vanilla

boring term sheet, you can pull off the internet because I'm not interested in cute terms. I'm not interested in anything that's gonna raise eyebrows in subsequent rounds. Like let's just stop dating right now if that's your mode is to try to sneak in some sort of Lickpref or otherwise like hard pass. I'm boring as boring can be on term sheets. And I'm very explicit about that from very early stages to...

to intentionally disqualify and like, let's just call it what it is. We're not a match. And this other term sheet that came in higher valuation, more capital, cute terms. And it was a hard no. I'm just an origin, lower valuation, less money, totally vanilla, plain Jane term sheet. So it's interesting demonstration that fund just didn't listen. And that in the end of the day, no thank you.

Jason Kirby:

Well, especially if you made it clear to them upfront that that's not what you want. And then they still came back.

Jen Henderson:

Yeah, absolutely. Glad I found that ahead of time, because I'd rather not find that out in a boardroom.

Jason Kirby:

And so that was the series A2. Was the series B next or was there other rounds in between?

Jen Henderson:

That was series A2, plus or minus 10 on that one. Series B came last year. That one almost tapped out. That was the most brutal, for sure.

Jason Kirby:

Well, Series B in the last three years has just been atrocious since 2022. So the fact that that's why I was like, oh, you're coming on. I was super excited to have you on because like, there's just so few companies that have crossed that threshold.

Jen Henderson:

I think.

Jen Henderson:

Yeah, we were almost one of the statistics, I'll tell you, in all transparency. I've been given the advice, as I think some of your guests have before I've heard of, well-run companies are always investable, right? Like, just focus on building a solid, operationally sound, clean company, and you'll always find the capital. I wish people would stop saying things like this, because it's it's mean. It's mean and it's not true.

It's not true. I've had responsibility of P &L since I was 21 years old. I know how to run a business, but that doesn't mean you're going to get the investment. And that's just, I think it creates false positives unnecessarily and mean.

Jason Kirby:

Well, it's also right, you know, what type of capital and on what terms like you can have a great business, but is that a venture business? Is it a private equity business? Is it a fire sale business? And if you're not in like, you know, for some businesses that kind of fell out of shiny object syndrome and VCU landscape in the last few years, it's just like capital dried up for so many well run great businesses. So I can totally empathize with you on that one.

Jen Henderson:

Yes. Yes.

Jason Kirby:

So guess what was your process like there? Like how long did it take? You know, how many people were you talking to? What was kind of the general feedback you were getting?

Jen Henderson:

The story that I'll share to start off the answer to this question is I had a founder tell me, Jen, if you haven't been in a bathtub at 2 p.m. on a Wednesday with a bottle of whiskey, you haven't hit rock bottom. And I'll tell you, I hit rock bottom with the Series B and that was an experience. The course of events that happened with the Series B is we got a term sheet after running a process of 100 nos to one yes.

this term sheet was exclusivity. So we were locked for three months. We rolled through the holiday season, locked and it expired and not a dollar was invested, not a dollar. They were pulling in other funds. It was more of a syndicate type structure. It was a lot of smoke and mirrors and pomp and circumstance, flying us out to Florida and having fancy dinners and the whole thing. We were completely snowed.

and come out of the exclusivity period and we were left starting over with three months of runway in the bank. So it was an absolutely terrifying experience of, holy shit, like we're restarting a process that we know takes nine months to a year in our historical data. And the first person I called was my Techstars contact. And we got the word out quickly.

and had, as you might imagine, an incredibly compressed process of a lot of phone calls and a lot of back-channeling and a lot of, here's the deck, here's the diligence, here's the data room, you want access, you've got access. And we met and got a new term sheet from our series B within 45 days, is what I'm remembering. And it was great, that was great.

good problem to have a progress on. The next part of the story I just can't make up and I'm nothing if not honest for your listeners if they at least find peace and shit happens to all of us, I promise. In the diligence, they found an error in our financial model and the error was modeling inaccurately so egregiously that they knocked 15 million off the top of the valuation.

Jen Henderson:

And it was justified. I get it that I would have done the same thing. But talk about a gut punch, I can't even, it's still raw, right? Like that is one of those punches in the face that you never see coming and nobody did it. My former finance leader just, it an error. It was an error. And that's life.

Jason Kirby:

Cool. Like, is it just like basically a KPI, like an assumption that was basically miscalculated that made it seem like, we're at a three X next year. And then reality was it was like, no, that's like a two X or one X kind of.

Jen Henderson:

Yep. I will give my series B lead a ton of credit. Number one, they didn't walk. Number two, they have made our, as you might imagine, hygiene around double, triple checking and being incredibly tight on our, particularly financial modding, but hygiene in general, which was already very well run. I said I'm an operator and I stand by that. They've made us better. And

Jason Kirby:

That is...

Jen Henderson:

maybe someday I'll look back and say, there's a silver lining in that experience. Right now, it's just, wow, that was scary days.

Jason Kirby:

Well, especially getting the report that they found that and then like the moments of are they still in? Are they out? You know, do you, are you one of the many other series B companies that go through something similar and just, you know, wind down after so much money, so much effort, so many amazing people working on something and to have it all fall apart over like one data point. So good as a them for.

Repricing, you know, hurts, but at least that was an honest valuation. would assume that, you know, was the Fed depologist, you know, was a kick to the face that doesn't feel good, but at you get to keep running your company.

Jen Henderson:

100 % and like I said, I don't fault them and we learned a lot from it. Now I will say to your point of another statistic that first term sheet that I shared with you that expired with not a dollar written, I absolutely bet your ass wrote that down of like what you have done to this organization in terms of impeding us from continuing the success that as a first time female founder, we're already

in the most infantile probability of existing, shame on you. Shame on you. And how you can expect anything but karma to come back. Like, I just can't wrap my head around it. Not only like, okay, the syndicant didn't come together, but to absolutely write not a dollar into this company that you've put us through this process, I have no words. And I certainly...

Jason Kirby:

Well, and to lock you into exclusivity when they don't have the means. they like a fun, a non-fun locking into exclusivity. That's, that's painful. It's just a warning to all founders out there. your, you know, do your homework and see what you can.

Jen Henderson:

100%.

Jason Kirby:

handle and do before getting into any kind of exclusivity. It's not uncommon to go into exclusivity after setting a term sheet, but make sure that capital is actually sitting at the bank account, especially when the market was an absolute disaster. Everyone was kind of promising they had money, but in reality, were trying, they're probably using you as leverage to go get money from investors and couldn't deliver.

Jen Henderson:

Yep. Yeah. Like I said, lesson learned for all of that advice plus a thousand. Yes. Definitely. Ask more questions. Learn from my mistakes because wow.

Jason Kirby:

You've been incredibly candid, and I apologize for bringing up what clearly is a sensitive topic. So maybe move on to a lighter topic in terms of talking about your experience in the HR tech space, with the advent of AI and just the general, I would say, slowdown and deals being done by venture in the last year or so. Where are you kind of seeing the industry go for HR tech?

Jen Henderson:

Yeah.

Jen Henderson:

Yeah, man, every day is a different answer to that question. would say where AI is going to really make monumental shifts first, I think is somewhat to be determined outside of the known administrative kind of co-pilot use cases. What we're finding unique possibly probably to HR tech, maybe you're seeing this in FinTech and HealthTech when you see PII and you see highly regulatory industries.

is while venture in particular is AI is going to take their lunch, AI is going to replace this, AI is going to be the next the new, right? How many times I've been asked, well, what is the AI first tilt equivalent being built in the basement coming out next week? Like, how does that hit your paranoia? Well, the reality is we know what can and cannot be replaced by AI in the work that we do today. That's not to say in a year and five years.

But HR, the buyers are not excited to buy a solution, in our experience, that is making decisioning from an AI agent. And we completely understand why. So while AI has absolute and indisputable efficiency gains, to the extent that it is making a decision in an HR tech application, there are barriers in place. And we get it. So.

We're watching obviously the market. We're trying to read the tea leaves as far as what's coming. We're absolutely respecting our buyers and saying, okay, like we're not gonna step around your CIO or whatever other provisioning that you're beholden to, but we'd get it. We deal with PII. That is not a small feat. So I think that there's an interesting...

An interesting conversation in the world of HR tech, HR tech investors and HR tech founders as to who are we really, first of all, who are we listening to? Our answer is always our customers, period, end of story. And how are we making sure that we're bringing our investors along in terms of learning what we're learning, challenging our thinking? We welcome that because we don't want to be myopic. But we're not here to push our buyers to

Jen Henderson:

engage in something they're not comfortable with today. So I don't know. I'm here for it. think AI is going to be revolutionary, but I don't know where HR tech is going to net out on it.

Jason Kirby:

think it's about point looking at the buyer profile and just the complexity of enterprise sales in and of itself. And then saying that you're going to give all your enterprise data to a startup to make decisions on its own accord. And then that employee, you're not selling to founders, you're not selling to high risk takers, you're selling to probably the more risk-adverse audiences out there.

And saying that like we're gonna replace either your job or what you think is important with an AI. It's like I'm not in love with this decision I'm not love with this product. will stick with my slow old software or whatever, know, whatever they're on or something like that where you know, they're gonna be less likely to to adopt also it's like we're in such a bubble because if you're in the tech space we have this a on that but like how many people are Thinking like that when they're you know, kind of between the

Jen Henderson:

Yes.

Jen Henderson:

Yeah.

Jason Kirby:

four walls of a big corporation that are often kind of set in their ways.

Jen Henderson:

Absolutely. And do I think HR tends to be, to your point, risk averse and sometimes a little behind the times in its thinking? Sure. But I think there's often good reason. But at the end of the day, if I speak very specifically to the space that we operate in, leave of absence is so personal. And I really am hard pressed to believe when the unthinkable happens and an employee loses a baby,

They don't want to talk to a fucking AI chatbot, period. I'm not sure if I might want to swear in your butt, but no. Like I won't, I will be hard pressed to believe it is all I'll say there. They need a beating heart. They deserve a beating heart. They need empathy and they need handholding justifiably to understand where they go from there. What do they qualify for now? How do they, are they out on leave or are they not out? Like to put that in a,

Jason Kirby:

I'll be back.

Jen Henderson:

call center or chatbot is just inhumane.

Jason Kirby:

Very valid point. That is a very complex and just the complexity of what drives lead. It's not just about having faith. There's all kinds of circumstances that force good talent to deal with complex situations outside of work and need maybe additional space for it. So I resonate with that. That's a way to look at it and also challenge those that think a vibe coded app with AI will be the next enterprise sales solution.

Jen Henderson:

Absolutely.

Jason Kirby:

And so other female founders that are out there, what would be your advice to other female founders that aspire to choose the venture path, go to Series B and beyond? And what would be your advice to them?

Jen Henderson:

Be successful. Be successful, because we have to win. We have to show we can put points on the board to start to effectuate 2%. And that is unfair. I get it. We shouldn't have to win every time, but right now in this moment in time we do. So figure it out. Don't give up and be successful, because we need it. We need to be able to show.

female founders behind us that you can't be what you can't see is real and we have to be successful.

Jason Kirby:

Bermier, you kind of shared some stories, but what would be some ways that you can tackle that yourself these days?

Jen Henderson:

you keep getting up. Like I said, we,

Jason Kirby:

Did you put down the whiskey bottle in the bath at 2 PM? Get back up.

Jen Henderson:

It depends on the day to so I reserve the right to pick it up. But the resilience and the connective tissue to the problem that you're solving, I think are two completely indisputable ingredients to continue to persevere and to be successful. To find like-minded people who get that it's different for female founders and help to be an advocate, to open doors.

for you when possible, to sponsor you when possible is really important. And to just recognize the game that we're playing. Like I put down the fight years ago that all judgment should be created equal because it's just not. And just because I kick and yell about it isn't going to change the current state. I need to be more intelligent. I need to come about effectuating change from a different angle. And today, that angle is be really successful.

so that Tilt can be a demonstration of it's possible and I can come to the other side of the table and start to invest and put my money where my mouth is because female founders outperform male founders on every report every year. It's indisputable. We put up better results. So that's where I want to put my money. And that is not to say my cap table is stacked with female investors. It's in fact not. Some of my biggest sponsors are male investors and we need them. We need them to be

champions and I have found some great ones that are champions. But to be naive to it and to just say, yeah, it's tough, it's not helpful. So we need people and I appreciate you giving me this airtime to come on and speak about it. Your newsletter was why I reached out is you see it, you know that this is not right. And anytime I get a microphone or a stage, I do it.

Jason Kirby:

been a powerful message and you know, for any founder, let alone a female founder to, to break out series B in the market that we've been in. And it just, it sucks. This is like all the macro forces against you on top of a solo female first time founder with kids. It's just like, you stack all those problems against you plus, you know, but the fact that you come out on the other side and hopefully it's continuous.

upward trajectory for you to a successful outcome. But that's why I wanted you on the show to kind of share that there are these stories of yeah, hell and back is possible. And you know, kind of be persistent. Nothing comes easy to you, especially in I just I got to throw some, you know, shade at the market right now. It's just been absolutely atrocious for for so many founders across the board. And for anyone that's making it out on the other side, it's pretty powerful.

Jen Henderson:

My heart just breaks for so many founders right now. My heart just breaks for them. This is brutal. It's Sorry. Like, what are we setting ourselves up for long-term, right? We're eviscerating this class of founders and startups. What's going to happen to this? I just, this is crazy times, crazy times.

Jason Kirby:

So.

Jason Kirby:

It's going be very interesting. There's one camp that says everything's going to get better because AI makes everything better. But then you look at the consolidation of technology resources and talent going to the big companies, Google, Microsoft, and so on. I see so many startups every day. And they're working on this really cool AI tech. But in reality, it's a feature that Microsoft releases six weeks later.

And it's just like, how are you going to convince, know, thousands, know, like hundreds of enterprise clients to choose you over Microsoft? And it's just like, it's such a hard landscape to be in. And there's going to be this, I fear, heavy consolidation in the market. And that's one belief. And then there's one, there's going to be hyper fragmentation. I think there'd be hyper personalization of content, experiences, media, things of that sort. But like,

software likely to be a heavy concentration consolidation into bigger companies. We keep talking about &A, it's going to explode at some point, it's starting to move a little bit, but I think just once liquidity comes back to market, will see more of it, but it's going to be very interesting in the coming years. Jim, what would you Yeah, nothing's boring in this space, that's for sure.

Jen Henderson:

Yes it will. Yes it will. We're never born.

Jen Henderson:

Yep.

Jason Kirby:

Heartbreaking, exhausting, and sometimes miserable when you question your existence, yes. Boring. So Jen, would be the best, someone who wanted to follow you, reach out to you, or see what you're doing at Tilt, what would be the best way for them to get in contact with you?

Jen Henderson:

Now we're at hellotilt.com. I'm on LinkedIn. Just search my name, Jennifer Henderson. I'm happy and active and actually respond. So happy to engage there if I can be helpful.

Jason Kirby:

Amazing. I'll make sure to put those in the show notes for people watching and appreciate you being on the show. Appreciate you being just candid and open about your experiences and what you've overcome and kudos to getting to how far you got. Definitely an amazing accomplishment.

Jen Henderson:

Thank you. Thanks for the time. I'm very grateful. Appreciate it.

Jason Kirby:

My pleasure.