SaaS Expert Voices presented by Maxio Randy Wootton, Maxio CEO

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Anthony Nitsos, Founder and CEO of SaaS Gurus. With a background that intriguingly intertwines medical school education and extensive expertise in finance, Anthony has over 25 years of experience building SaaS financial models. Randy and Anthony discuss principles for building and scaling backend financial systems that can transition from startup to scaleup without creating a "tech pile." By drawing parallels between human anatomy and business functionalities, Anthony emphasizes the significance of a single source of truth in accounting systems and the critical nature of precise and actionable data for organizational leadership. 
Quotes
“If your spine and your core muscles are not strong, the rest of your body hanging off of that isn't going to be. The same thing works in the back office of finance systems. You need to have a rock-solid accounting system that ties to a rock-solid forecasting system that both feed into a KPI system. That is our three-part, financial core.” -Anthony Nitsos [17:00]

“One big challenge is creating that one holistic view of the customer and product data that then helps inform not just the statements, but also the operating reports that you're using to run the business. Understanding what's going on with churn, understanding what's going on with retention. There are some exceptions, but you have to go and figure it out, you have to recode it. I think early-stage companies are just scrambling to get product out.” -Randy Wooton [14:39]






Expert Takeaways 
Interconnected Thinking: Addressing root causes and systemic connections in finance and operations in SaaS companies.The Financial Core: A strong, streamlined accounting system tied to a precise KPI system is crucial for providing actionable intelligence to executive teams.Tech Stack vs. Tech Pile: Creating a proper technology stack rather than a disjointed tech pile for seamless data flow and informed decision-making.Cash is King: Accurate cash flow forecasting is paramount and enables CEOs to plan effectively for growth or investment.Building Valuation: The ultimate objective of a CFO in the venture-backed SaaS environment is to assist companies in growing their valuation and preparing for successful exits or investor rounds.


Timestamps
(01:20) Anthony Nitsos: Applying medical training to problem-solving
(08:57) Preventing, detecting, and correcting in-process optimization
(13:30) Need for a unified customer list for integrated analysis
(19:05) Providing actionable intelligence as a strategic enabler
(26:13) The significance of accurate revenue recognition for SaaS companies
(34:30) The CFO: “Cash Flow Oracle”
(41:06) Projecting cash and analyzing it
(47:05) What is the mission of the CFO?

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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Jeff Epstein, Operating Partner at Bessemer Venture Partners and a distinguished figure in the business and finance sectors. Randy and Jeff discuss the rationale behind budgeting, emphasizing its role in predicting financial futures, resource allocation, motivation, and maintaining fiscal discipline with investor funds. Jeff talks about the recent introduction of the Rule of X by Bessemer Venture Partners, examining the balance between growth and profitability. Jeff also shares pragmatic wisdom from his time at Oracle about setting realistic yet ambitious targets and flourishing within set constraints.

Quotes
“I think the Rule of X is my favorite metric because it combines revenue, growth and profitability. There is always that tension and that trade off. Should we grow faster and invest more or should we try to get more profitable sooner? And both the CEO and the CFO, that's one of the key resource allocation decisions they make. Another way to think about it is it's short term versus long term. You need to do both. You need to both achieve your goals this year and build the company for the long term. And the Rule of X captures both concepts.” -Jeff Epstein [40:21]

“I think the way we think about that, and I'm only going to B2B SaaS guy, is what is the pipeline that has to be built to match the capacity, the sales capacity? So street quota, what is that? So for using an example, like 10 million bucks, marketing sales have to be totally aligned in terms of how many dollars need to be invested in paid surge versus events, et cetera, to create the pipeline, the days to close and the percent win rates that gets you to an 80/80 hit. So I think that's a great rule of thumb.” -Randy Wootton [25:40]




Expert Takeaways 
Rule of X: a nuanced approach to evaluate a company's performance by combining growth with profitability.Budgets serve as a predictive tool, a resource allocation guide, and a motivational scorecard, and are fundamental for fiscal discipline, especially when using investors' money.The importance of aligning annual budgets with a company's strategic three to five-year plan and the careful management of board expectations.50/50 probability when setting revenue targets should ideally lead to aggressive but achievable goals.Executive compensation strategies: balancing individual accountability and sharing in company-wide success.


Timestamps
(01:28) Jeff’s time at Oracle
(03:06) Building budgets
(06:37) The Rule of X
(09:09) The relationship between strategy and budget
(16:00) The need for more evidence before relying on AI efficiency improvements
(21:00) The 50-50 rule for team performance
(29:17) The three-part compensation plan and the alignment of incentives with profit goals.
(32:48) Driving incentives and motivation through MBOs and OKRs
(36:02) Addressing the tension between annual budgets and actual performance


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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Dawoud Nasraty, Director of Consulting at Armanino. After serving as an accountant at a Big Six firm, Dawood's career trajectory includes roles for a European telecommunications company in Afghanistan and as a CFO. Dawoud and Randy talk about the intricate world of data and decision-making, the technological advancements shaping accounting practices, and lay out the essential lessons and best practices drawn from Dawood's extensive stint as both a consultant and an in-house financial controller. They also discuss the necessity of solid infrastructural investment and why startups often fail without robust financial systems. 
Quotes
“Sound metrics built on sound data. And a lot of companies that get started, not all, but a lot of them, in the beginning, don't pay as much attention to the back office, the finance, and accounting. So it's important, like finance and accounting takes like second or third place, but it's important to establish a solid foundation in that area sooner than later, not too early, but not too late. So the CFO, the CFO needs to encourage investment in the finance function at different stages in the company's life cycle.” -Dawoud Nasraty [18:18]“Someone once said to me that the number one deal killer in M&A is accounting issues and that's because companies haven't done the work, hiring professional consultants, advisors, fractional CFOs to come in and help put the systems in place so the data works and so that they can represent the reports.” -Randy Wootton [11:41]



Expert Takeaways 
 Establishing strong finance and accounting foundations early is critical for startups to manage reporting and withstand investor scrutiny effectively.A coordinated system of record is essential for assembling a 'single source of truth' that facilitates accurate decision-making.Overlooking the importance of meticulous financial management and data integrity can lead companies toward a wind-down state.Implementing effective technologies can change the game for SaaS companies in aligning with sales teams and managing cash flows.Learning from failures and 'worst practices' informs better approaches and readiness for future business challenges.

Timestamps
(00:39) Dawoud’s background
(06:10) Working with a startup company and setting up accounting systems
(12:29) Good data and its role in statistics, finance, and economics
(18:08) Sound metrics are built on sound data
(24:21) The challenge of transitioning from spreadsheets to a solid tech platform
(29:08) The impact of revenue recognition on business metrics
(31:11) The need for a thoughtful approach to data management

Links
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Dawoud Nasraty LinkedIn

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with David Nilssen, CEO of DOXA Talent, and a forerunner of revolutionizing how businesses think about and engage with borderless talent. Randy and David take a look at the intricacies of borderless talent acquisition and the attributes that contribute to the success of a CEO in today's ever-evolving SaaS landscape. They discuss how purpose-driven approaches to outsourcing can bring about positive global change and how talent scarcity, remote work, offshoring, and AI integration are altering the business world permanently. David also talks about the value of peer groups and why you need to invest in your tribe. 
Quotes
“The interesting thing about the Guidant business is that we don't make a tremendous amount of money financing businesses. That's what we're known for. But we actually really try to break even, as you're pointing out, on that particular deal. And then we have tax and accounting, payroll and 401K administration on the back end. And so what's really interesting about that business is that we've figured out a way to acquire a customer, profitably acquire a customer and then provide them with other services that really has no acquisition cost associated with it.” -David Nilssen [30:32]

“How do we operate at the edge of our own ignorance? How do we keep learning and how do we have enough humility to ask? Because part of the thing I think as a CEO is people look at you for the answer and sometimes you don't know what the answer is. And so you got to admit that you don't know and then go ask questions of everyone you can. Like what you're describing with learning about subscription businesses and how that model works, is going to help you be a better leader and create a better business.” -Randy Wootton [42:22]






Expert Takeaways 
The talent landscape is being reshaped by four key trends: talent scarcity, the rise of remote work, the necessity of offshoring, and AI advancements.Creating a meaningful employee experience is crucial for retention and productivity, particularly in remote work settings.A focus on 'impact' and 'income' helps secure a sustainable career progression for remote employees, generating value for both the employee and employer.Peer groups provide valuable support for personal and professional growth, benefiting not only business leaders but also their interpersonal lives.Today’s CEO: curious and open to learning, embraces their role with humility and has a keen sense of responsibility.

Timestamps
(01:46) Trends in talent scarcity and remote work
(04:31) Challenges and advantages of focusing on SMB and mid-market
(10:50) Creating a culture of purpose, leadership, team, client, and career
(17:05) The value of career pathing and continuous learning for employees
(22:19) Tracking the key metrics
(30:38) Investing in your tribe: mentor, coach, peer group, and peer advisory
(34:56) How to be a CEO: learning and humility
(37:26) EO, peer groups, and investing around you
(42:16) Success: curiosity, ownership, and a people-first mentality




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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Dave Boyce, a GTM-focused SaaS Advisor, board member for Winning by Design and Forrester, and professor at BYU. Dave shares his unique approach to career decisions, focusing on his need for challenging work that ensures personal growth and impact. This approach has shaped his strategies for businesses to adopt a customer-centric mindset that aligns the product with the user's core needs, creating a successful PLG strategy. Dave and Randy discuss the framework required for a PLG model, identifying the mindset, talent, and timeline necessary for successful adoption, and how go-to-market strategies differ and can coexist in today’s business environment.
Quotes
“There are three really hard pills to swallow. One is mindset, one is talent, and one is timeline. For mindset, I'm going to get in an empathy and generosity mindset where I'm simplifying down and meeting a customer right where she is. I'm going to put metrics into the product so that when she's stumbling or not making her way through, I'll know about that. Because I don't have a human in the room anymore either selling or implementing or coaching or training. That customer is on her own and I need to know when she's having trouble. Empathy, generosity, and metrics help me get that user experience right.” -Dave Boyce [08:33]

“PLG introduces this low threshold of payments that are tied to value. I think that creates discipline in your marketing motion. It creates discipline in the way you think about satisfying customers' pain with your claim, the delivery of the capabilities, and how you do fast iteration and improvements. So I think it's this dynamic constraint or mixing of two metaphors, but you've got these constraints in terms of your business model and what you can afford to do, and that makes you super scrappy. So it is in line with innovation, fast fail, rapid turn type motions.” -Randy Wootton [14:47]




Expert Takeaways 
PLG strategies focus on the product selling itself, with immediate value creation for users as opposed to the typical sales involvement in SLG.Go-to-market fit requires a scalable and economical source of customer acquisition, aiming for a customer acquisition cost (CAC) payback period of less than one year.Scaling PLG into a viable business unit involves understanding a growth model dependent on new customer acquisition, renewals, and expansion.The dynamic between PLG and SLG isn't necessarily an 'either-or' scenario; they can and often do function as complementary strategies in a hybrid model.

Timestamps
(02:03) Guiding principles for career pivots
(10:23) Differentiating between bottom-up and top-down approaches in PLG
(13:41) Adapting to PLG with a lower ACV
(21:29) The false dichotomy between PLG and SLG, the hybrid approach
(26:00) Rolling out a PLG business: product-market fit, go-to-market fit, and scale
(32:35) Designing applications to get product usage metrics
(42:41) Building a flywheel and repeatable processes for PLG
(44:47) CAC payback for unit economics and discipline

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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with CJ Gustafson, CFO, and writer behind Mostly Metrics, to discuss the CFO's transformation from a back-office statistician to a front-office strategist, the evolving landscape of SaaS, and the future of finance leadership. Randy and CJ discuss the qualities that distinguish outstanding CFOs, the integration of strategic planning with finance, and the powerful impact of technology on the CFO's role. Listen as CJ shares how CFOs are leveraging technology to streamline processes, enhance decision-making, and drive company performance while balancing risk in the dynamic SaaS sector.

Quotes
“I think there's a lot of idea generation that's made easier and then being able to link together different areas of work. So there are a lot of cool tools that are coming about that will take, basically information from the front of the house, from customer support, or maybe like a BDR, getting information to then link and say, does this person have an account with us? What's their historical spend? Have we ever talked to them before? It's linking data from different parts of the organization in a way that you can tell a story and then go back and have a conversation with the customer, which I think before would have taken a lot more time.” -CJ Gustafson [40:38]

“Being deeply integrated with the CEO and the CRO in terms of monetization strategy, I've talked about that as moving from the back office to the front office. What pricing should we be using, and packaging should we be trying, for which segments, for which products, in which regions? How does it impact our win rates, and how does it impact our churn? That, owning pricing and being able to provide options and being willing to experiment.” -Randy Wootton [08:33]


Expert Takeaways 
Good CFOs are distinguished by their role as chief resource allocator, chief truth-teller, and chief risk officer, balancing strategic investments and maintaining honesty in communication.Modern CFOs must effectively integrate operational and financial data analytics for strategic insight, which demands both a high-level "eagle" perspective and a detail-oriented "mouse" focus.The evolving fintech stack and advancements in AI are enabling finance teams to elevate performance, with tools like Maxio automating revenue reporting and aiding in strategic planning.As technology proliferates within finance functions, a key challenge for CFOs is to ensure that tools are adopted and add value, rather than merely becoming shelfware.AI in finance is less about creating standout performers and more about raising the baseline performance of a team, but vigilance is necessary to avoid data "hallucinations" and inaccuracies.




Timestamps
(01:26) Qualities that separate good CFOs from great CFOs 
(06:18) Evolution of the CFO role and moving from back office to front office 
(13:13) Empowering the management chain and setting up monitoring systems. 
(22:15) Tailoring metrics for different audiences 
(26:35) The importance of planning in preparation 
(30:37) One database or data lake for production, operational, and financial data. 
(35:10) Improving both people and technology. 
(42:27) Creating guardrails and running AI models multiple times for accuracy. 
(44:39) The evolving role of the CFO and embracing augmented intelligence




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