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The Funding Blueprint: Unlocking Startup Success artwork

Navigating Hiring Challenges: How to Identify and Nurture Talent with Jenny Weeden

The Funding Blueprint: Unlocking Startup Success · 2025-12-04 · 28 min

0:00--:--

Key moments - from our scoring

Substance score

36 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality6 / 20
Guest Caliber10 / 20
Specificity & Evidence5 / 20
Conversational Craft6 / 20

Jenny Weeden draws on nearly a decade at Milwaukee-based Accelity to offer founders practical guidance on scaling teams sustainably. She argues that early process documentation - even simple one-pagers - prevents founders from becoming bottlenecks and enables consistent customer experience as the company grows. When it comes to hiring, Weeden advocates for intensive vetting rather than defaulting to the best candidate available; she introduced an internal alignment document before opening positions to clarify actual needs and success metrics. She and founder Jackie discovered that the visionary-integrator framework from Entrepreneurial Operating System (EOS) explained their partnership: Weeden's role as the person who "gets shit done" complemented Jackie's big-picture vision. Red flags include misalignment between words and actions, excessive politicking around decisions, and ignoring hiring concerns just because of a good relationship. On firing, Weeden acknowledges the difficulty of moving fast when relationships are strong, but emphasizes that delayed action creates team confusion and conflict - and that affected employees often find better fits elsewhere. For founders beginning to scale, she recommends using freelancers strategically before committing to full-time hires, seeking self-starters who thrive with autonomy, and investing heavily in first-line managers who can multiply your leadership capacity.

Key takeaways

  • →Documenting processes early as simple one-pagers prevents founders from becoming single points of failure and enables consistent team onboarding and quality as the company scales.
  • →Hire for long-term fit rather than selecting the best candidate available; use an alignment document defining skills needed, success metrics, and culture fit before recruiting.
  • →The visionary-integrator partnership model clarifies complementary roles; identify integrators who challenge you, treat the business like their own, and align on core values rather than mirrors of yourself.
  • →Red flags for partnerships and hires include misalignment between stated values and actions, over-politicking around decisions, and ignoring concerns simply because of a good relationship.
  • →Moving slowly on necessary firings creates team confusion and conflict; while difficult, timely decisions ultimately benefit the departing employee, remaining team, and company culture.

Guests

Jenny Weeden

Topics in this episode

Entrepreneurial Operating System (EOS)Process DocumentationEmployee retention strategiesAccelityVisionary-Integrator partnership modelHiring alignment documentationFreelancer vs. full-time hiringTeam culture fitRed flag detection in partnershipsLeadership scaling

Questions this episode answers

Why should founders document processes early if they're already busy scaling?

Documenting processes prevents the founder from becoming a bottleneck, ensures consistent customer experience, and creates a baseline for new hires to learn from. It doesn't have to be elaborate - even one-pagers are better than nothing and actually speed up growth in the long run.

How do you identify someone from within the company who could become a partner?

Look for an 'integrator' who complements your visionary strengths, someone who treats the business like their own, stays aligned on core values, and is willing to challenge you. Watch for consistent values alignment over time and someone who walks the talk rather than just talking the right things.

What's a practical way to avoid hiring mistakes when you have limited candidates?

Create an internal alignment document before hiring that specifies what skills are needed, what success looks like in 6-12 months, and culture fit. This prevents hiring the best candidate available when they're not the best fit for your actual needs. Also do a final step after reference checks where you voice any concerns before offering the role.

What early signals suggest someone might not be a long-term fit at the company?

Watch for missed deadlines, disengagement in meetings, unexpected time off patterns, and shifts in attitude - though these can sometimes be phases. Having another leader to discuss observations with helps determine if concerns warrant action.

Should you hire a full-time employee or use a freelancer when scaling?

Evaluate whether tasks are easy or hard to teach and whether you enjoy doing them. If a task is easy to delegate but you dislike it, consider a freelancer. If there's sustained full-time work and you need cultural integration, hire an employee. Freelancers avoid the responsibility of employment while still filling gaps.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

There are a handful of useful tactical nuggets - the pre-hire internal alignment doc, the skill-will matrix for deciding between freelancer and FTE, and the observation that early hires often reflect 'best of available' not 'best fit' - but the episode is padded with broad platitudes and meandering anecdotes that dilute the useful-per-minute ratio significantly.

we hired the best fit of the candidates we had and not the best fit for us
we added an internal alignment doc. Before we even started hiring, we asked, what do we need? What skills? Why are we hiring? What does success look like in 6 to 412 months?

Originality

6 / 20

The episode leans heavily on widely circulated frameworks (EOS Visionary/Integrator, 'hire slow fire fast') and general wisdom ('treat the business like your own') with no meaningful contrarian argument or first-principles thinking; the 'peanut butter to your jelly' framing is a relabeling of EOS content, not original insight.

find the peanut butter to your jelly
We run entrepreneurial operating system, uh, which people call EOs

Guest Caliber

10 / 20

Jenny is a genuine practitioner who grew from employee #3 to partner at a real operating company, which gives her credibility as an operator rather than a thought-leader; however, Accelity is a small regional agency and the scale of experience discussed is limited, keeping her well below the threshold of a heavyweight operator.

when I started at Accelity, I was maybe employee number three
she was basically like, hey, you're doing this thing like you're owning, uh, our marketing automation software

Specificity & Evidence

5 / 20

The episode is almost entirely anecdote-free in terms of hard data: no revenue figures, no headcount numbers, no client names, no retention percentages, and the guest explicitly declines to get specific on the hardest examples; vague phrases like 'incredible retention rates' and 'bigger clients' substitute for real evidence throughout.

I won't get into anything too specific
now we get like hundreds of resumes

Conversational Craft

6 / 20

The host asks predictably sequential follow-ups ('building on that,' 'kind of shifting here') and never challenges a claim or asks for a number, a specific client, or a counterexample; affirmations like 'yeah, absolutely' and 'that was amazing' dominate the transitions, producing a PR-friendly chat rather than a probing interview.

Yeah, definitely. That was amazing.
Absolutely. So, kind of building on that

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B79%
  • Speaker A21%

Most-used words

team17jackie14processes13building11hiring10feel10founders9jenny9early9sure9hire9partner8point8alignment8grow7start7

Episode notes

Jenny Weeden discusses the critical importance of process documentation in the early stages of business growth, emphasizing that many founders overlook this step due to the multitude of responsibilities they juggle. This oversight can lead to bottlenecks, inconsistencies, and a single point of failure, ultimately stalling growth and varying quality across customer experiences. Jenny highlights the necessity of starting with simple, one-page process documents to create a foundation for smoother onboarding and consistent operations. She recounts an inflection point at Accelity when the absence of process documentation initially created challenges, but once implemented, it significantly improved the onboarding experience and allowed the company to scale more effectively. Reflecting on her journey to becoming a partner after nearly eight years with Accelity, Jenny offers insights into what founders should consider when bringing on a partner, especially from within the company. She advises looking for a complementary dynamic, such as the visionary and integrator roles, where the visionary provides big ideas and the integrator executes them.

Full transcript

28 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Welcome back to the Funding Blueprint, the podcast where we dive into the real strategies founders use to build, fund and scale startups from the ground up. I'm your host, Cece Neheman, and today I'm joined by Jenny Whedon, president and partner at Accelity, a Milwaukee based agency helping scaling companies across North America grow with confidence. Jenny has been with Axelity for nearly a decade and now leads the charge on business operations, team development, and culture, all with a sharp eye on sustainable growth. In today's episode, Jenny and I will unpack what it really looks like to grow inside a company, from a team member to a partner, and how founders can build more intentional companies. Along the way, we'll talk about the power of documenting processes early, the lessons she's learned through firing and hiring, and how to vet the right people when you're bringing on partners. So whether you're building a team, defining your operating rhythm, or trying to grow sustainably, Jenny brings a ton of operational wisdom, um, and honest perspective you won't want to miss. Let's get into it. Jenny, welcome to the show.

Speaker B: Hey, Cece, thanks for having me.

Speaker A: Of course. We're so excited to have you. So let's just jump right into it. Let's start with process. You've said that one of the most valuable things a company can do early on is to document their processes. Why do you think founders tend to overlook this?

Speaker B: Yeah, I mean, founders wear so many hats, right? Like, I, when I started at Accelity, I was maybe employee number three. And I recall, um, like, even then wearing like ten different hats. Yeah. So think about then what the founder has to go through. It can feel like. It can feel like a luxury to be able to sit down and write down processes, and it can feel counterintuitive to the growth and the pace and the building energy that is at hand when you're starting out and when you are at the door of scaling and you don't have processes, that can be a problem. Uh, you become a bottleneck for everything. Growth can stall, there can be inconsistencies in customer client experience. Quality can vary. And like, when you don't have that baseline for process, it can impact the business in ways that you're not thinking of. Um, because everything's in your head, you become like the single point of failure at times. So documenting processes early may feel counterintuitive, but it actually speeds you up in the long run.

Speaker A: Absolutely. So, kind of building on that, what's a lightweight way for an early stage founder to start Documenting without feeling like they really need to build a full SOP playbook.

Speaker B: Yeah. Um, well, when I started, Jackie had no processes, and so she was basically like, hey, you're doing this thing like you're owning, uh, our marketing automation software. Just like, bullet point or like, put. Put a one pager together of, like, how you do certain things. It's kind of like building the. The plane in the air. You don't have to feel like you're doing it all at once. It can be like, I. I'm doing this thing, and after I do it and maybe learn from some failure or success, I'm just gonna put a one pager together so I have notes. It really doesn't have to feel like I'm writing a novel. It could just be like, I have something down. I have a starting point. And Jackie always told me early on, I would rather have something to start with than stare at a blank page. So it can be that simple.

Speaker A: Yeah, absolutely. Building on that a little bit more. When did you realize that process documentation was a turning point at Acceleraty? Can you share a moment or an inflection point when not having documentation created at that bottleneck?

Speaker B: Yeah, I mean, when I first started, because we had no processes, and Jackie basically said, I need you to learn these things about the business and then document them, because she did not have the capacity to do that. And I kind of. My role at the time was marketing coordinator, whatever that means, wearing, you know, the 10 to 20 hats I was wearing. Um, but I was like, all right, let me Google what that means. Uh, and then we were very scrappy back then and kind of dove into it. So right away I was like, all right, having something's gonna feel good because I'll have a standard. And then I think where it really hit, where I was like, oh, this is valuable, is when we hired next, and I was like, oh, they're not gonna have the same kind of experience I had, because there's a baseline for them to come in and learn where we're at and what we're doing and what the expectations are. Um, so knowing that, and actually what I've seen is my processes weren't that good to start with, but they were something, right? They were a starting point. And as our team has gotten better, the processes evolve. And then the processes evolve to a point where we're helping level people up. And so now the processes are incredible. They align with, like, a higher quality, uh, for our. That our team exudes. Like, our team is just way more experienced than they were when I first started out. And we have, uh, are getting bigger clients because of it. Like the processes evolution has really allowed us to grow more. So starting simple and early really helped.

Speaker A: Yeah, that's amazing.

Speaker B: Yeah.

Speaker A: Kind of shifting a little bit here. You became a partner after nearly eight years with the company, which is beyond impressive. So from your perspective, what should founders look for when they are bringing on a partner, especially someone from within the company?

Speaker B: Yeah, find the, I'd like to say find the peanut butter to your jelly. Um, we run entrepreneurial operating system, uh, which people call EOs. Uh, and in that system, um, there's the idea that there is usually a visionary or head of the company. And there's also, um, the integrator. Jackie was looking to find her integrator. Um, and so what that means is the visionary is the idea person, the relationship person, the um, big picture thinker. And I don't know if I'm allowed to swear on here, but I would say I came in as the integrator, the person who gets shit done. Right. Like you're the person who says, cool, got all those, like, big ideas. Which one do you actually want to do something with? I'm going to actually make sure that happens. Um, and so she needed that. And I think the, in that relationship, if you founders, I would say, tend to relate to the visionary, or V, we call it more than the I. If you're that visionary, you, you want to find someone who's going to challenge you. Six years ago, I was not ready to do that. I was building my challenging muscle. Um, you need. You might as well hire a mirror then. If you. For as your integrator, if you don't want to be challenged, um, making sure that you're in alignment for sure and giving each other grace and respect, I think all of those things are super important. And if you start identifying that in somebody and at your business, then they, they could be the, the integrator to your vision.

Speaker A: Definitely. Yeah, kind of. I guess in addition to becoming that, you know, integrator, that building up that challenging muscle, what's some other advice that you would give to someone within the company who wants to become a partner? How do they showcase themselves in their challenging moments over time?

Speaker B: I would say, and I'll probably get into this more later too, but, um, one thing that always stood out to me, that Jackie told me over and over again, was you treat my business like it's your own, even though you have no stake in it. And so if you can find out what's important to the owner and treat the business like. Treat the business. The business finances like it's your own. Think about, like, I would say, hey, I have this idea, and I. Here's how I think it would be incorporated. And I know, like, X, Y, and Z factors might work against us, but, like, here's what this looks like. When you start showing owners and founders that you're treating the business like it's your own, they can take you seriously when the time comes.

Speaker A: Definitely, kind of. Again, building on that a little bit more and what you discussed, let's now talk about the values alignment aspect of this. What were some of the key indicators or even those tougher conversations that helped you and the founder determine that you are aligned long term as partners?

Speaker B: We have been aligned for a long time, and we could sense that we would be in leadership meetings together, and I'd express an opinion, and Jackie would say, uh, I am completely in agreement with you on that. And then we'd, like, loop back after the meeting and be like, yeah, we're really on the same page here. Or a lot of Jackie's decisions. I would. There might be pushback at times, and I'd be like, actually, I completely agree with this, and I'm on board. And, like, I would help other people get on board as well. Um, we'd often say, let's just, like, short. We'd have, like, shorthand of, like, same page. Or we'd send each other the brain emoji to be like, same brain. Um, and I would notice when she was out of office or maybe busy, or maybe you'd have, like, a greener employee who was afraid to ask her a question. Um, people would come to me and be like, well, you can read Jackie's mind anyway, or whatever. They'd be like, you guys must have talked about this already, because we. She pro. She said the same thing later. And I was like, we never spoke about this. We were always in alignment on the big things. We don't agree 100% of the time. That's okay. That'd be, again, hire a mirror. Um, but we just were really aligned on the same things. And I think that is because I. Not in a weird way, but I like, study people, and I want to know what's important to them. I figured out what was important to her and her business. I decided. I agree with that. The value she has on hard work and treating people with dignity and making sure that everyone has a seat at the table. I was like, yes, those are the values. I agree with. And so when the time came, I'm like, all right, I can treat this business like it's my own because I'm fully in alignment with her. Um, and that does make it easier to then position yourself to be seen as a possible partner. But, yeah, definitely.

Speaker A: Obviously, you and Jackie seem to have an amazing relationship.

Speaker B: Yeah.

Speaker A: On the flip side of this coin, are there any red flags you think founders should be on the lookout for when evaluating potential partners?

Speaker B: Yeah, I would say. Well, of course, I think it's super simple. But walking the walk that you talk, um, when I've seen where people are like, you know, they'll say the right things, but then the actions don't match. And especially in a small business, that's really easy to suss out because it's incredibly transparent. Um, and that type of thing doesn't usually. I mean, you know, someone could get through like that, but I think you've got to really, really be watching out for that because ultimately it's not going to be a good fit for either person. Yeah. When the time comes for decision making, and I think, like, when people, and I might talk about this a little bit later, but when people politic too much, when there's been a decision made, and then people keep trying to revisit and dig up the grave of the decision that's been made to be like, well, what about this? It's like, no, we have to have people rowing in the same direction. When Jackie and I are in full alignment, I feel like we are rowing together and we haven't like, thrown our paddles off the boat and said, you do all the work or stuck our paddle in the water to say, I'm going to slow us down now. Like, when you're feeling friction, that's a red flag to me of like, there's not alignment. What's going on here?

Speaker A: Yeah, absolutely.

Speaker B: Yeah.

Speaker A: Kind of shifting a little bit here. You've had a front row seat to the hiring and the firing process as the accelety team grew. A lot of people say hire slow, fire fast, but in actual practice, that can become challenging. So what mistakes did you make early on in hiring and what did they teach you about the process?

Speaker B: So many, um, so many. I think a big one for us just starting out when we were first starting to hire is we hired the best fit of the candidates we had and not the best fit for us. Like, I specifically recall we were kind of unknown. Um, now we get like hundreds of resumes. I'm like, drowning in resumes. Anytime we hire but when we started out, we were less known. There were fewer people applying, so we maybe got like 10 or 20 resumes. Like three or four looked good. We interviewed three to the final stage, and we were like, well, of those three, this one was the best. So let's hire them. And it turned out that, like, they weren't the fit because we were hiring the best of what we had. Instead of thinking, like, all right, how can we think outside the box? Who else can we speak to? Or, like, how else can we get this out there? And what does that look like? That's hard when you're trying to save money, when you're trying to be scrappy and all of those things. But, um, that was a big one M for sure. And now we hire the right fits. We go through an intensive process, and that keeps our retention up, which is obviously beneficial. Then you're not replacing all the time either. Um, we've also ignored red flags. Speaking of red flags, um, we have hired people who maybe, like, weren't a fit for our culture or wanted things that we just couldn't offer or provide. And I don't want somebody to feel like they're trying to make do with what we can offer. I would rather call that out. So we've ignored red flags in the past, which leads to bad levels of retention. And ultimately, what we've decided to do there is we have a specific spot after the final interview and before we do. And actually, I think after reference checks as well. And we say we're 90 to 95% sure this is the person, but we gotta talk about all the concerns that we might have had. And we have not hired people in that final step because we felt that they wouldn't be happy with what we could do or vice versa. Maybe they weren't a fit. Um, because we just. Our retention is really important to us. We have incredible retention rates, and they've only gone up in the last four years. And it's like, I just don't want to mess with it. So. So, yeah, um, I think those are a few things. One thing I'll say is, uh, to fix a lot of those issues, we added an internal alignment doc. Before we even started hiring, we asked, what do we need? What skills? Why are we hiring? What does success look like in 6 to 412 months? Um, a whole bunch of other things I'm not thinking about right now. But doing all of that is super helpful to think ahead and be really feeling good about the type of people we do and don't need. To be speaking with.

Speaker A: Yeah, definitely. I love that. On the contrary here. Firing is one of the hardest parts about leadership.

Speaker B: Yeah.

Speaker A: So can you talk about a time you didn't move fast enough to let someone go and how that could have affected the team or the culture? Yeah.

Speaker B: Ah, I won't get into anything too specific, but I think the hardest times for firing are when we have great relationships with people and then, um, the fit's just not there as much anymore. Whether we grow as a business because change is constant and, or they just grow in a different direction or they need different things. Um, think example scenario would be like, you know, there are times when Jackie has to make really hard decisions. She's the CEO. She hears out all sides of an argument and at the end of the day, she must make a choice. Um, and it's not going to make everyone happy all the time. Uh, and in those scenarios, I don't always agree, but I can agree or disagree and either way I commit. That's my job as a leader. That's a responsibility I have and I don't want to be the person putting the paddle in the water and slowing us down. I think at times like that there have been times where maybe some people disagree and decide not to commit. And that's where kind of the toxic politicking comes up, comes into play. Um, and so if we can't get to. There have been times where we can't get to an alignment and I think we've dragged our feet. Feet because of the relationship. Um, and ultimately the best news in all of this is when we do get to that point, accelety is better for it, the team is better for it, and, um, the former employee is better for it. We have so many former employees who are like, I found my dream job. Or like, this was actually like a great thing that happened, was me, um, moving to something that felt like more of a fit. But in that moment when that's all happening and we're not taking fast action, the team is confused. There's high conflict, you know, there's friction. It can get messy fast.

Speaker A: Absolutely.

Speaker B: Yeah.

Speaker A: Building on that just a little, what are some cues or signals you. You now may recognize early that tell you someone might not be a long term fit, even if you have an amazing relationship with them?

Speaker B: Yeah, uh, our team is so good right now. I'm like, I have to think about this. M. When, uh, I think it's like common things, but like when deadlines are getting missed, I'm like, where's your head at In a kind way. Like, yeah, of course. Are you doing okay? Yeah. Or like, what's going on? If, um, if I'm showing up to meetings and like people are kind of doing other things, I'm, um, like, what's going on? I, I think often when we see people taking random like time off, we might. Sometimes Jackie and I think, oh, are they, are they looking elsewhere? Like, are they feeling good here? Um, and yeah, I mean some, sometimes these signs show up like aggressively.

Speaker A: Yeah.

Speaker B: And. Or like you can just sense like a different, a shift in attitude and sometimes like kind of come out of the blue. Um, or are like so mild, you're like, oh, this might just be a phase. So, um, that's a harder, that's a harder thing. But I think the thing I will say is being a partner at the business, like having Jackie and Jackie having me to talk about these things we can have. Again, we're not looking in a mirror. We're talking to another person who has a different perspective to be able to say like, should I be worried about this? Or is this, do we think this is just a phase? Or whatever? And so like noticing differences and how someone is showing up, uh, being able to speak through that and to.

Speaker A: That is helpful 1,000% to kind of wrap things up here. You've helped grow Axcelody from a small agency to a company that serves clients across North America. From an operations and leadership standpoint, what advice would you give to founders who are just starting to scale a team and feeling overwhelmed by all the people stuff?

Speaker B: Yeah, um, first of all, I would say, do you need an employee, do you need a full time employee or do you need a freelancer or a virtual assistant? I think some people jump to, I need a part time or full time person. But we can get creative with solutions. And one of the things we do that I think is helpful because we, we scale that way, we don't just automatically hire team members. We often use freelancers to fill gaps. Especially if we don't. Especially if we know we don't have the work to hire somebody full time. Because hiring an employee is a lot different than hiring a freelancer. There's just a level of responsibility there that you don't have with freelance or a virtual assistant. Um, and so making a skill will is something we do where we say how easy or hard is the task to do and, or teach? Um, and how much do I hate doing it or love doing it? And if you start there, you look in the easy to do or teach and I Don't like doing it quadrant you might find. And you could look in the hard and don't want to do it path too or whatever. But um, when you look in those, if you see trends of like, well, this feels like admin work that can guide your direction or this feels like it's specific to a specialty, um, maybe you do need a freelancer. But if it's like this is, if this is enough work for a full time person, then bring them on. And I would definitely recommend saying you need a scrappier self starter, especially if you are first hiring, looking for people who can figure it out on their own, who don't need much hand holding. As a founder, you really don't have time for that. Um, and I say that as one of the people who was on the ground floor and had to figure it out on my own, I was fine with that. Find people who want to do that, um, because they can see the benefit of being here long term. I'm an example of that. Um, and highlight what the benefits of that are, I think. Also don't try to hang on to everything and make sure expectations are super clear. Like you want to be so clear in what this person should be doing. Um, because you're going to do a lot less firefighting later if you have that, um, spelled out. A couple other things I would say is if you do have a manager, like a general manager already on the team and you're looking to build from there, invest time in them, resources in them, hold them accountable, like teach them how to be kind of like a you, like maybe like ground level, you first, like first line of defense, you, um, because. And like train them on the culture. You want to see all of those things. If you can invest in that person, they're going to be able to scale and take on more of the responsibility and just know that like leading and building a team is about people. And it might feel again counterintuitive to put time into people and give feedback and listen, but you are turning from a single source to a force multiplier. And so being a force multiplier means feeding your people with your time. Um, and frankly, after a while you water the garden a little bit less and you can still see more results. It's just that kind of ramp up period. So yeah, I think that's probably enough to share.

Speaker A: Yeah, definitely. That was amazing. And unfortunately that wraps up today's episode of the Funding Blueprint. A huge thank you to you Jenny for joining us. We covered a lot of ground from the benefits of documenting processes early to what it really looks like to vet a business partner, and the lessons Jenny's learned about hiring slow and firing fast while growing a high performing team. Her insight into the operational side of scaling a company was referring to refreshingly honest and packed with real takeaways for any founder or operator building for the long haul. Be sure to check out the amazing work Jenny and her team are doing at Acceleity, especially if you're a scaling company looking to drive serious growth. And if you enjoyed this conversation, make sure to subscribe, rate and share the Funding Blueprint with a fellow founder or builder. We've got a lot more tactical behind the scenes episodes coming your way soon. Thank you so much again, Jenny. And thank you so much for listening everyone. We'll see you next time on the Funding Blueprint.

Speaker B: Thank you.

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