The CFO Secrets Every Founder Needs to Scale Profitably with Heather Hall

Most founders don’t have a marketing problem.

They have a financial visibility problem.

In this episode of The Takeover, we sit down with Heather Hall, founder of Sapphire CFO Solutions and former CFO across multiple fintech and SaaS companies, to break down what separates scalable businesses from the ones constantly stuck in survival mode.

Heather shares the behind-the-scenes realities of startup finance, from messy books and cash flow stress… to fundraising, data rooms, forecasting, and preparing for exits.

If you’re a founder, operator, or agency owner trying to grow with clarity and confidence… this conversation will completely change how you think about finance.

Keynotes & Chapter Markers:

• 00:00 – Heather’s journey from audit to startup CFO
• 08:38 – Why founders delay finance until it’s too late
• 11:28 – The importance of visibility & transparency around numbers
• 16:39 – Building a data room and preparing for an exit
• 24:13 – The ROI mindset CFOs use when evaluating investments
• 29:57 – Why thought leadership matters for modern founders

Connect with Heather:

LinkedIn: https://www.linkedin.com/in/heatherhallcpa/
Website: https://www.sapphirecfosolutions.com/

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About The Hosts:

• Tim & Cindy Dodd are the Co-founders of PEMA.io, based out of Miami, FL. Connect with Tim and Cindy on LinkedIn and Instagram:
  • Tim’s LinkedIn, Tim’s Instagram
  • Cindy’s LinkedIn, Cindy’s Instagram

About PEMA.io:

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Transcript

00:06
Welcome to The Takeover with Tim and Cindy, where we show you how to dominate your market.  Let's get winning.

00:17
What if the reason your business isn't scaling isn't your marketing,  your sales or your team,  but your financial infrastructure?  Today's guest has sat in the CFO seat across some of the most dynamic companies in fintech,  HR tech and financial services.  She has taken companies from pre-seed  all the way to exit.  She co-founded a fintech startup that pioneered transparency in the bond market.  And she's done it across public companies, private enterprises and startups.

00:47
She's the founder of Sapphire CFO Solutions,  a board member, CPA, chartered global management accountant,  FINRA principal, and a Princeton and Wharton alum.  But what makes Heather Hall different is that she doesn't just read the numbers.  She builds the systems, aligns the strategy, and sits at the table where the real decisions get made.  If you're an entrepreneur who wants to stop running blind  and start scaling smart,

01:15
this conversation is for you.  We dive into everything juicy around finances, exits, and what you need to be doing in your business in order to scale with profitability.  Welcome to the show, Heather Hall. Thank you, Cindy. I really appreciate the invitation. It is going to be a fun conversation. always say that, know, finance can be boring, but finance can also be fun. So I like to call it fun-ance. So we're going to have a lot of fun.

01:43
talking about CFO solutions, what you will do, um and specifically how business owners, marketing and sales leaders  can truly tap into the power of what finances can do. So before we get into all the juicy bits, let's take us back to the beginning, how you got started in CFO work and what keeps you passionate about this work today?  Sure. So, you know, I started my career off

02:11
in 1994 as an auditor.  And I thought, you know, it's my very first professional job.  I had my sights on becoming an audit partner,  really like the firm I was with. But, you know,  after a year or two, I just realized it wasn't dynamic  enough for me.  So I wanted to take that base knowledge  and, you know, use it essentially out there.

02:40
within the financial services industry. That's really what I focused on at the audit firm and just really liked it. And so, after I left, it's like, well, gosh, what do I want to do? And I definitely had my sights set just on that top job. It was a goal. I'm very, very goal oriented. So.

03:04
You know, I just spent my career  working towards that and finally got uh my first CFO role in 2008. I  was working for a private registered investment advisor  in the Bay Area. was based in San Francisco and still am frankly for over 30 years. And so I started off there. uh I also

03:30
became head of HR. So that was really not by choice, but something that I was given. And that was a real challenge, almost even more than the finance role, because HR is very specific, right? It's regulatory driven and particularly here in California. So I had this dual role. They had some management changes in 2016. So I was actually laid off and

04:00
At that point, you know, it's just doing that recalibrating. Okay, where do I want to go next? Really liked the  CFO role. And so I thought, you know,  I've worked  through my auditing career  with kind of big public companies. Now I've done the small private. I thought, you know, I really want to do a startup.  And so I reached out to my network. I was introduced. uh

04:26
to a bunch of guys and they had an idea. So it was just a concept where they wanted to create the first cloud native platform to buy and sell bonds. Needed a CFO. They were very excited also about my HR experience. So literally met with these guys on Friday and then Monday I had the job. that was a lot of work, but just so much fun because

04:52
you're just really creating something  from scratch. And that's really when Cindy, I realized, gosh, I really like tech. I like it because it's just continually evolving. You're constantly learning. And I just found it to be very exciting. um And so through that role, we ended up, I was there for about, let's see, five years, and then we ended up merging with an investment bank.

05:22
And I got a new role  at the newly merged company where I was a chief administrative officer managing director  of the entire tech division and just loved it.  I definitely, was kind of like the CFO of that division,  but then all of these other  responsibilities, which  I  just really enjoyed. I like working with people and I'm a firm believer that finance should not be siloed.

05:50
You really need to integrate it into the fabric of the business.  And this, that role really allowed me  to do that because I was liaising with just different organizations or really functional  areas across the business. So, know, legal,  HR, you know, the corporate finance group, m product, m just everything.  You know, and I think also through

06:19
you know, to what I'm really passionate about, you know,  when I worked, when we first founded  the startups, 280 cap markets,  I did a lot of networking uh with other founders, other CEOs  in and around  the Bay Area. And what I really saw through that experience is that startups are really great with products and services, but they struggle with financial infrastructure,  struggle with cash flow.

06:49
a lot of times with fundraising and exits. And I always like to say that, know, numbers tell a story, but I feel like most founders have never been taught to read it. And so that's what I'm passionate about is really, I feel that I can make a difference by structuring the number story  behind the growth.  So I created Sapphire CFO solutions really to bridge that gap  and just find it really rewarding to work with startups and

07:18
bring them the clarity, the confidence they need with respect to the finance infrastructure. So a lot of times, right, it can be intimidating.  And I like to break it down and really show how you can use finance as a strategic  lever for your business. It's not just a reporting compliance function. It really shouldn't be viewed in this review mirror, if you will.  Again, just looking at it.

07:45
as this lever to grow the business. Wow. You've had such vast experience, right? All the way from working with startups to large corp. You've seen the back end  of so many organizations. What would you say is the biggest mistake you see founders or teams make around their finances?  Sure. I think, you know, it goes back to they just see it as this reporting compliance function.  And so what I found when I've gone in,

08:15
either  someone on the team who's not a finance person but has familiarity, say with QuickBooks,  they're doing the books. QuickBooks is always the go-to. Who even knows how to do QuickBooks? is. is. it's, you know, it's,  like the UI. It's,  you know, they make at least QuickBooks online. It's easy for folks  if you're not a finance person  to use  for the business.  But  so you have that or...

08:44
you have like a bookkeeper that really isn't well versed with like particular revenue pronouncements that you need in like a tech enabled or SaaS business.  And so I find,  just, again, they just don't see it as a strategic function.  And then oftentimes,  all of a sudden they  need to do a raise, right? And so,

09:12
they need a data room, they need the financial modeling, then it's like, they're almost out of, it's like you run out of options, that's what I find. You put finance on the back burner, and then all of a sudden your backs against the wall, and you need a strong finance function like yesterday, and then you bring someone in and it takes time.

09:36
100%. Oftentimes there's a lot of cleanup, right? With the financials and the books that needs to be done. And I'm just coming in kind of late in the game  and it's really just,  we need this immediately when, you can get it done. um But again, I like founders  and CEOs to have optionality, right? Because then you...

10:05
You can make better decisions. not,  again, you're just, you're not out of options.  So it is just helpful. I find that when you feel that there's a growth story to articulate, that's a great time  to bring in  your CFO, whether it's  fractional or it's  somebody that you hire in-house.  Because again, you really want the numbers to be able to  tell that growth story.

10:32
That's what investors are  going to look for. So good, so good. it's like  when finance is not  a specific function or it's kind of put on the back burner, from what I'm understanding is that for CEOs and founders, it limiting your options, right? You kind of don't know, you don't have full visibility into what's really happening in your business.  And when there's big decisions that need to be made,

10:58
you're limited because of the information that you have, right? If you're limited on information, you're limited on options. love that you mentioned that. You know, I will also add on to that as well. You know, I see a lot of teams, there's no visibility or transparency around the numbers. So you have, you know, key members of the leadership team, just say like, you know, your head of marketing, HR and...

11:25
they're just not privy to the whole financial picture. And I think that's, it's really important to share that with your team because  you want to show, you know, the leadership team, well,  here's the decisions that you made and here's the effect on the bottom line. You know, you, that's going to help them, right?

11:48
improve. It's also very positive, right? If things have  been done right and really just have affected the business in a positive way and you want to share those wins  with your team.  So that's another thing that I've seen,  or talking to different functional areas across the org,  they  have no idea  where the business is at, where it's going.

12:13
what impact decisions that they've made have had  on the business.  So I think that's another thing because  you want to keep, especially in startups,  Everybody's working really hard. um You've got multiple hats  and you want to really create that positive environment and keep morale up. Yes, absolutely. Transparency and visibility around the numbers. On that note, how often should

12:40
teams, leadership teams be reviewing and looking at their numbers? So, you know, it depends. I personally like setting a cadence and meeting once a week. You know, it doesn't have to be this long, you know, detailed meeting. But what you're really doing is you're setting up the process, you're setting up  the cadence and you're really creating like a good mindset,  you know, around finances, around the numbers. So I think, you know, meeting weekly, starting off with wins for the week.

13:10
And then just discussing, hey, here's where we done. Are we still  on track to meet our monthly KPIs, even milestones that go further  down the road?  I think it's really helpful.  Once a month, especially in a fast pace environment, it's not enough. I feel like you need to meet more frequently.

13:33
So I would say at least twice a month, but I really like the weekly meetings. And oftentimes they don't have to be an hour. If you have set it up correctly, you can get through it in half hour or so. And then everybody's aligned and there's, you avoid miscommunication down the road. Everybody, hey, this is what it is, this is what we're doing next. And then you have to follow up at the next meeting.

14:02
I love that. That's definitely something that Tim and I have implemented as well. For those of you that  follow the show and follow us, you know that we have our weekly Friday Founders Sync happens every Friday. That's a time for us to align. But part of that 15 minutes in that one hour block is just for finances, right? We're looking at our numbers.  I love that you mentioned celebrating wins. that's something that we do at the start of the meeting as well.  So it may be sometimes like, hey, we're not where we want to be. But what are the positives, right? What's going well?

14:32
In what areas of the business do you maybe cut expenses or do you this revenue growing? So I think finding the wins, spotting the wins is so important. And then as you're mentioning, creating those action items and next steps so that  one, there is visibility, but everybody is aligned.  And I think often too, when you do celebrate the wins,  it's often easier for the team to say, well, what didn't work so well?  Because you're not.

14:59
they're not on the defensive. It's a very, you open collaborative  meeting. And I feel that it oftentimes puts team members at ease to share, well, hey, this isn't going well, you know,  what can we do here?  And you're in this big meeting with, with leaders  across the organization and people have helpful, helpful insight to offer. Absolutely. Absolutely. So we have a lot of entrepreneurs that listen to the show and I know the

15:28
big kind of goal on a lot of founders mind is the big exit, right? So how should founders and teams be preparing for an exit from a financial or finance perspective?  Sure. I mean, I say the first thing to do,  whether or not you're preparing for an exit  is to create a data room. And so, you know, in the data room, you're going to have key documents, those that relate to compliance and governance.

15:57
like our articles of incorporation, the basic legal docs. You want a set of financials, your financial model. It's really a way to kind of get everything organized. And then when you really are ready for that exit, you have the bare bones down and it's just, it's really helpful. And I also think that once you have that established, it's there, you're gonna continue to add to it.

16:25
because  that's really important to have just a strong data room with everything in there. You're not scrambling to find documents from  two, three, four, five years prior. It just makes it difficult, right, as you  continue down the road. But  from a finance perspective, uh you wanna have a clean scrub set of financials. Like, as I say,

16:52
often audit ready. A lot of the startups, you're not paying for an audit, that's fine, but you want a strong set of financials that are audit ready. And then your financial model, that's really important. And I like models that really include a scenario analysis. So you're not just presenting the space case. You also wanna look at a downside case and an upside case. You wanna model with levers.

17:22
that you can pull. Well, what if I change the price on this particular product?  What happens if we increase headcount, decrease headcount, and those changes flow through the model so that you understand, well, if I pull this lever,  if I pull X, then Y happens. So you do want a good strong financial model.  I also recommend for startup, these financial models,  they do provide a cash forecast, but

17:49
Is that super specific? Because you're really imputing cash by using a three statement model. So I often recommend to pair with the financial model like a 13 week cash flow.  And we always call these 13 week cash flows because 13 weeks approximates a quarter.  So you'd have all this historical  cash behavior.  And then also you have a uh really nice quarterly projection of what cash looks like.

18:18
you know, out in the next quarter. And I often find that's really, really helpful in particular for startups, right? A lot fail because you run out of cash.  Not that you didn't have a great idea, but you know, they're just extremely cash sensitive.  So I often find that having that 13 week cash flow model to pair with a financial model, those are great. Obviously you,  I mean, it's kind of goes outside of finance, but you know, there's other things that you'd want in your.

18:47
your data room, your marketing plan,  you want your product roadmap, things like that. So while those fall outside of finance, they touch  on finance. Again, going back to my point, Cindy, that  finance should not be siloed, right? It should integrate across  the business.  It just, to me, I just don't see it as anything other than that. Definitely. And as you're preparing for an exit, you definitely want a CFO in your corner to help you work through.

19:15
All of those specifics that you are mentioning Heather, absolutely. When I think about  some of  us at Pima, we sell to mid-market enterprise organizations and  some of our  clients that are marketing agencies are selling in these spaces as well.  When we are say pitching to a team,  very often the final real decision maker is the CFO, right? Once we get CFO approval, then we have the full approval.

19:43
So give us the CFO insights, give us that perspective. What is a CFO looking for  when bringing on say a new marketing vendor or potential marketing plan or strategy?  What are you all looking for? Sure, so I mean, I'm looking for  ROI. I wanna see, okay, we're having this spend, but then, you know, what's the outcome? What are the benefits? What's the ROI? I wanna definitely make sure that we're not just like,

20:12
plugging a gap. So let me let me give you an example. I had a client again. Cash is just very tight, you know, from month to month. Their cash flow positive, but just barely.  So Stripe offers these. It's almost like a cash advance.  They charge a fixed fee. So let's just say you want to borrow $250,000. They'll  give you, hey, this is going to be your fee. It's almost like an interest, if you will.

20:42
but it's fixed, this is what you're gonna have to pay, and we're gonna pull it out of your revenue monthly. So my client had already taken a Stripe loan, it worked well for them, it's almost paid off. So they came to me and said, hey, I  just got another offer from Stripe to take out another loan, what they would do is they'd refinance  what's left on our existing loan, package it all together,  what do you think? And I said, well, I wanna see,

21:11
specific priorities that we're gonna be  using that money for,  and I wanna see the ROI generated.  Like, well, we really just kind of use it to pay down AP. And I said, well, we're just plugging a gap, and you're just almost exacerbating the problem.  So  again, just,  I wanna see like, how are we gonna use that cash? And I wanna see either,  I would work with the leadership team.

21:40
Well, let's create projections. You know, again, it's almost like a mini model, a mini scenario analysis on,  okay, marketing team, you want to use this, I don't know, say you a service that  you're outsourcing your BDR, something like that.  Well, historically, you know, have these BDRs worked in our industry and kind of, you know, what's their historical performance? What does it look like?  And then we can create.

22:09
generate some scenarios  from that data. Well, here's baseline, here's the best they could do, here's the worst. What does that look like?  And are there other options? Like have you researched other providers? m Or why are you just bringing this particular team?  Why are you evaluating just this team?  Have you looked elsewhere? What are some other options out there?  I just want to make sure that we're

22:38
we're going to get a return  off of this investment. And then are there other alternatives that we've researched that potentially could be better options for us?  So good. That right there, ladies and gents, I think you need to rewind  and re-listen to that again, Heather. That was so much value.  And what I'm hearing, and we've seen this in the sales process as well, is  ROI, ROI, ROI.  What  does ROI look like when this company spends money with you?

23:07
It's not just as Heather is mentioning to plug in a gap, right? It is to produce an output.  And as the salespeople, as the people that are selling the service, it is our job to ensure that we are very clear on what that output is going to look like.  And of course, right, being in marketing, we know that there is the component of the salespeople have to do their part, but we have to do our part as well.  And I love that you mentioned that too, Heather, which is a company is going to be looking at various other potential vendors.

23:36
And when we can make it easy for them to see that we are like the obvious choice, right? Through things like here's the ROI, here's people that we've worked with in your space before, here's the output you can expect.  It makes it a lot easier for us to get the yes and the okay  from the CFO. So that was  so much value. Yeah. I mean, it's,  I, it just seems very, very clear to me that my client, they ended up not going with.

24:04
the loan and what's interesting is the CEO, he got it. uh Probably not the answer he wanted to hear, uh but he got it. And then interestingly enough, I had the board member of that same company, he didn't know that I had the conversation with CEO.  He was asking, hey,  could we potentially get another Stripe loan? And I said, oh, I had this conversation with, we'll just call him Steve.

24:29
the CEO and I just shared  basically the transcript of my Slack conversation.  He was just really happy. He goes, really great point. He goes,  get it. So,  yeah. I love that. So good. Let's shift gears a little bit. know that we work together on your visibility.  Let me tell you, actually backtrack. When a founder is thinking about being visible online and you post a lot of thought leadership type content, right?

24:58
Is it uncomfortable to start to be more visible for somebody that maybe isn't as comfortable with it? How do you balance being visible online with running your service based business?  Sure. Well,  I really want to,  I want to like me personally, or are we talking in general? Oh, you personally. Me personally. Yeah. Visibility.  So I think that you, it's all about establishing that cadence. I think, you know, again, you

25:27
I want to be seen as a thought leader in this space. I have a lot of experience. I feel like I have a lot of value to add. I find it really rewarding when I get comments to my posts like, hey, Heather, that's a really interesting way to  look at this problem, this issue.  But I need to establish a cadence and really take time to be thoughtful about my posts and to be visible. And  you need to be consistent. It's not.

25:57
You can't just post, say, for three months. I almost think it takes at least 12 months.  And you need to be very consistent about it. Again, think  for me, it's establishing set  times  and set days  where I'm really going to focus on it. And a lot of times, sometimes it's uncomfortable.  And I say this because I'm being vulnerable.  But it's like that's-

26:25
I want to be real and it's not all about the wins, right? It's like, hey, here's what didn't go well.  I think  it's all part of the journey, but  here's what I did.  Here's what happened. This didn't go so well. And here's how I pivoted. And here's what I did to circumvent that and to  try to minimize my exposure to that happening  once again.

26:52
I really like LinkedIn.  For me, I've tried outbound, it doesn't really work. And I kind of look and think, well, gosh, I see what I do when I get these unsolicited messages. I think for me, LinkedIn is definitely the place to be because you can establish your authority as a thought leader and people are going to hopefully remember you, remember your posts when the time comes  when they need your services.

27:21
You know, they're going to remember, oh,  I remember, you know, that post that Heather did, I'm going to reach out. Yeah, for me, it's really kind of living in LinkedIn.  But there's just so many,  you know, interesting people on there. I mean, I learn a lot from reading posts oh from others and, you know, everyone has perspective and  value uh to add.  Heather has an amazing profile, amazing content. Definitely check her out on LinkedIn.

27:50
Let's talk about that Heather, who is your ideal client for those that are thinking about potentially bringing you on to CFO walk us through a little bit more about your services  and how people can get in touch.  Sure, sure. So I decided when I went out on my own, to be honest, I was thinking about maybe pursuing the cannabis vertical because there's so much business there. ah But I ultimately through conversations within my network who introduced me to some folks in that vertical.

28:19
I ultimately decided to stay in my lane and focus on financial services, SASS and tech enabled businesses. uh And  again, I look  at really pre-seed through series B. That's where I have the experience. So that's my focus. So it's growth companies in that space.  Again, financial services, SASS and tech enabled sectors  and helping those businesses. That's really where I feel.

28:48
I can add the most value. Amazing. And your services overall, give us a bit of a CFO, give us a little bit an overview around your services. Sure. So I do really kind of the whole suite of CFO services. I do also have an accountant on staff so I can help clients that have an accounting need. So have that on my team. But the CFO, I really focus on FP &A, so financial planning analysis, so all the financial modeling.

29:18
oh capital allocation, fundraising,  due diligence, things of that nature. work both  on, Cindy, I do both hourly and then  retainer based. And I like to work with companies,  in terms of pricing, really like to see  where companies are at. Because  sometimes  it's different, the needs and the pricing if you're  pre-seed versus a  series A or series B, those tend to get more.

29:47
complex.  Yes, absolutely. So if you are in that growth stage, ladies and gents, make sure that you reach out to Heather  and her team. I definitely reach out. And then this is our last question here. Then we ask all of our guests this on the show.  What does winning mean to you? I think winning is  for me, it's really  leaving things at a better place than when I found them. You know, I like to  think of it.

30:14
gonna nerd out here on the accounting outlet. I call it the lasting balance sheet, right? It's like a legacy that you leave behind. It's about  courage, conviction, having values and living by those values.  That's really kind of the lens that I bring to Sapphire. And again, after you're gone, it's that lasting.

30:42
lasting balance sheet. It's the legacy that you leave behind. I  think that it's important to focus, you know, it's not just like  the bottom line and growth. It's about relationships and people.  And I think that's really important for potential prospects. Like  I ask about that because I want to work with founders that have a value system and have that established. That's very important to me and very, very meaningful.

31:11
So I want to work with  like-minded uh individuals. Amazing. This was such a great conversation Heather. Thank you so much for joining us on the show. And I know that our listeners found so much insight from you as well. So thank you. Thank you, Cindy. Thank you. Thank you so much.  That's it, ladies and gents. I hope you enjoyed this conversation as much as I did and that you got value from the show.

31:35
If you did, would you please leave us a comment  and leave us a review wherever you are listening to the show. It helps so much.  Connect with Tim and Cindy Dodd on LinkedIn, our favorite platform, as well as all the other social channels we want to hear from you. Drop us a note, send us a DM. We'd love to connect.  Always remember, domination is not a destination. It's a way of life. Stay winning.