#87 - How to Hire and Develop a COO: Building Your Second in Command

In this episode of Millions Were Made, Jessica Marx and Brooke Dumas discuss how founders can set strategic and realistic revenue goals for 2027 based on data, profitability, market conditions, and business capacity.They explain why revenue planning should go beyond choosing an ambitious number. From reviewing historical performance and evaluating offers to understanding team capacity and the investment required for growth, Jessica and Brooke break down what founders should consider before setting their next revenue target.Together, they discuss:Why revenue goals should be based on strategy rather than an arbitrary numberHow historical and forecasted data can inform future revenue targetsWhy profitability is an essential part of evaluating business growthWhat declining revenue can reveal about offers, marketing, and sales strategiesWhy businesses should identify the cause of declining performance before pursuing aggressive growthHow market research and changing consumer behavior influence revenue planningWhy significant growth often requires additional investmentWhen maintaining revenue may be more strategic than increasing itHow personal priorities and founder capacity should influence business goalsWhy reducing owner dependency creates greater flexibility within the businessHow to determine whether your current team can support your revenue targetThe true costs associated with hiring, training, and expanding capacityHow pricing, headcount, and profitability can create different paths toward the same revenue goalWhy profitability may need to improve before a business is ready to scaleHow scenario planning can help founders choose a growth strategy that aligns with their long-term goalsIf you are setting your goals for 2027, this episode will help you build a revenue target around what your business can realistically support and where you actually want it to go.Listen to the full episode of Millions Were Made to learn how to approach your 2027 revenue planning with greater clarity and strategy.Mini-timeline00:00–01:57 — Why founders need a strategic approach to setting revenue goals for 202701:58–05:22 — Using historical performance, profitability, offers, and market data to determine realistic growth05:23–07:08 — Accounting for seasonality and evaluating revenue decline07:09–10:59 — Identifying the underlying causes of declining business performance11:01–14:15 — Why ambitious growth requires strategy, investment, and infrastructure14:16–17:58 — When increasing revenue should not be the primary business goal17:59–21:32 — Profitability, owner dependency, and aligning business goals with personal priorities21:33–25:21 — Evaluating team capacity and determining whether a revenue goal is operationally achievable25:22–27:08 — Using business data to model different growth scenarios27:09–29:37 — Revenue rules, hiring costs, the Tailored business audit, and the 2027 Business Planner29:38–31:02 — Four key steps for setting a strategic 2027 revenue goal and final takeawaysResourcesFollow @millionsweremade on Instagram for frameworks + strategy tipsDownload the 2027 Business Planner: https://astounding-founder-8808.kit.com/products/2027-business-planning-bundle Explore the Tailored Business Audit Example to help you evaluate your numbers, capacity, and growth strategy for 2027: https://tailoredpremier.com/business-performance-assessment Connect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored Premier Website: Millions Were Made

In this episode of Millions Were Made, Jessica Marx and Brooke Dumas discuss what it takes to build and develop a strong number two who can lead effectively, take ownership, and reduce dependency on the founder.Hiring an experienced COO, integrator, or second in command is only the beginning. Jessica and Brooke explain why even highly qualified leaders need time to understand a founder’s vision, communication style, expectations, and approach to decision-making. They share how intentional onboarding, clear feedback, and explaining the reasoning behind decisions can help a number two develop greater confidence and independence.They also examine the founder’s responsibility in creating a successful leadership dynamic, from establishing clear communication expectations to teaching operational leaders how to present strategies with the right data and context. Ultimately, developing a strong number two is not simply about making the right hire. It is about building the trust, alignment, and leadership structure that allows the founder to step away without the business depending on their constant involvement.Together, they discuss:What makes a strong number two beyond experience and qualificationsWhy personality and communication style matter when hiringWhat founders should expect during the first three to six months of onboardingHow explaining the “why” behind feedback develops stronger decision-makersWhy founders need to establish clear communication expectationsHow to train a number two to present strategy with relevant data and contextWhy previous work environments can influence leadership habitsThe importance of distinguishing genuine business issues from unnecessary emergenciesWhy even the right hire requires ongoing developmentHow founder and leadership alignment can reduce owner dependencyIf you have hired a COO, integrator, director of operations, or second in command but still find yourself involved in every decision, this episode offers a practical look at what may be missing and how to develop a leadership structure that can operate effectively without your constant involvement.Ready to reduce owner dependency and build a leadership team you can trust? Listen to the full episode of Millions Were Made.Mini-timeline00:00–02:43 — Why developing a strong number two is essential for reducing owner dependency02:44–05:34 — Jessica and Brooke’s working relationship and what makes an effective second in command05:35–06:57 — Why personality, communication, initiative, and leadership style matter when hiring06:58–09:03 — The learning curve involved in onboarding an experienced operational leader09:04–11:46 — Why the first six months are critical for establishing expectations and independence11:47–13:44 — How effective feedback and explaining the “why” support long-term development13:45–16:29 — Teaching your number two to communicate strategy and present decisions with supporting data16:30–18:16 — Unlearning previous workplace habits and distinguishing problems from emergencies18:17–20:21 — Founder responsibility, emotional regulation, and establishing clear communication expectations20:22–23:26 — Why even highly qualified hires require ongoing coaching and development23:27–25:18 — The Number Two Training Program and strengthening founder–operator alignment25:19–25:55 — Final takeawaysResourcesFollow @millionsweremade on Instagram for frameworks + strategy tipsNumber Two Training Program: https://bit.ly/4rKQbYl Connect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored Premier Website: Millions Were Made

In this episode of Millions Were Made, Jessica Marx and Brooke Dumas discuss why founders should begin planning for the coming year well before January and how early strategic planning can create stronger financial and operational visibility.Following their private client retreat in San Diego, they share how founders can use Q4 to evaluate business performance, secure future revenue, refine offers, and establish clear priorities for the year ahead. Jessica also explains why these decisions should be guided by data rather than emotion, particularly when revenue slows or growth begins to plateau.Together, they discuss:Why annual planning should begin before JanuaryHow to secure future revenue through renewals and annual agreementsThe value of entering the new year with committed revenueHow to evaluate pricing, profitability, and existing offersWhy stagnant growth does not always require a new offerHow data can guide stronger strategic decisionsWhat to evaluate across your offer suite, lead journey, systems, and client experienceHow AI and changing consumer behavior should influence planningWhy founders need dedicated time to operate from the CEO levelHow proactive planning can reduce owner dependency and create greater freedomIf you are preparing your business for 2027, this episode will help you evaluate where you are now, identify what needs to change, and build a more intentional strategy for the year ahead.Listen now!Mini-timeline00:00–02:15 — Why Jessica and Brooke begin planning for the coming year before Q4 is over02:16–04:28 — Why waiting until January can put founders behind their competitors04:29–07:40 — Using renewals and deposits to secure revenue before the new year07:41–09:24 — Creating an implementation timeline without overwhelming your team09:25–12:21 — Using business data instead of emotion to guide strategic decisions12:22–15:13 — Evaluating your offers, lead journey, systems, and client experience15:14–17:06 — Why strategic planning remains essential at every stage of business growth17:07–19:52 — Creating the time and space to operate from the CEO level19:53–21:28 — How proactive planning supports greater freedom and reduces owner dependency21:29-22:14 — Business Planner resource and final takeawaysResourcesFollow @millionsweremade on Instagram for frameworks + strategy tips2027 Business Planner: https://astounding-founder-8808.kit.com/products/2027-business-planning-bundleConnect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored Premier Website: Millions Were Made

In this episode of Millions Were Made, Jessica Marx and Brooke Dumas explore how founders can increase the long-term value of their businesses by building sellable verticals.Many businesses unintentionally combine multiple services, offers, and revenue streams into one structure, making it difficult to scale efficiently, market clearly, or create future acquisition opportunities. Jessica breaks down how separating key areas of a business—from service divisions to intellectual property—can improve profitability, operational clarity, and overall enterprise value.Using real client examples, they discuss how strategic restructuring can help founders create cleaner financials, stronger brand positioning, and more flexibility when it comes to future growth or potential exits. They also unpack common mistakes businesses make when layering new offers into existing brands without a clear operational strategy.Together, they discuss:What sellable verticals are and why they matterHow separate business divisions create acquisition opportunitiesThe importance of clean financial tracking and operational structureWhy branding and marketing clarity improve conversionsCommon mistakes founders make when combining multiple offersWhen it makes sense to create separate entities or brandsHow intellectual property and licensing increase company valueWhy founders should think strategically about AI and future scalabilityIf you’ve ever added new services, programs, or media brands into your business without a clear structure, this episode offers practical insight into building a company designed for both growth and long-term opportunity. Listen now!Mini-timeline00:00–01:25 — Introduction to sellable verticals and why founders overlook them01:26–05:40 — Accounting firm case study: separating tax strategy, accounting, and preparation services05:41–06:43 — How vertical separation creates future acquisition opportunities06:44–09:42 — Functional health practice example and separating credentialing programs from operations09:43–11:31 — The biggest mistakes founders make with IP, branding, and financial allocation11:32–14:02 — How unclear business positioning creates marketing and sales problems14:03–16:14 — Can businesses have too many verticals? Strategic expansion vs. unnecessary diversification16:15–17:38 — First steps founders should take when restructuring business verticals17:39–18:57 — AI, future-proofing, and identifying the most valuable assets in your company18:58–End — Final thoughts and founder takeawaysResourcesFollow @millionsweremade on Instagram for frameworks + strategy tipsConnect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored Premier Website: Millions Were Made

In this episode of Millions Were Made, Jessica Marx sits down with sales strategist and founder of The Salesgirls, Macy McNeely, for a practical and insightful conversation about the hidden sales gaps that prevent businesses from scaling sustainably.Many founders believe inconsistent revenue is a marketing problem, a lead generation issue, or a systems breakdown. But according to Macy, the deeper challenge is often much more foundational: most entrepreneurs have never intentionally learned how to sell. Instead, they rely on momentum, passion, referrals, or strong offers—until growth plateaus and the existing approach no longer works.Throughout the episode, Macy explains the difference between simply making sales and truly understanding sales psychology, persuasion, buyer behavior, and messaging. She shares why many multi-six and multi-seven-figure business owners continue to leave significant revenue on the table despite having established audiences, successful launches, and experienced teams.Jessica and Macy also discuss how modern sales environments have shifted. Buyers are more skeptical, more discerning, and more resistant to vague messaging and overly complicated funnels. As a result, businesses must become more precise in how they communicate value, build trust, and guide prospects through the buying process.Macy also shares real examples from her own business, including how a highly targeted 23-minute sales message generated nearly $300,000 in revenue by directly addressing the specific resistance buyers were experiencing in real time.This episode offers a clear and actionable perspective for founders looking to improve conversions, strengthen their sales process, and scale their business with greater clarity and confidence.Listen now!Mini-timeline00:00–02:00 — Introduction and why inconsistent revenue often points to deeper sales issues02:01–05:30 — Macy’s philosophy on selling before building and creating offers alongside clients05:31–09:30 — The difference between making sales and truly understanding sales strategy09:31–12:30 — Buyer resistance, objections, and the psychology behind conversion12:31–16:30 — Common breakdowns within sales systems and lead nurturing16:31–20:00 — Building belief before asking prospects to buy20:01–23:30 — Founder mindset, sales leadership, and company-wide influence23:31–27:30 — Hiring salespeople: what founders often get wrong27:31–30:30 — Training sales teams and aligning them with founder vision30:31–32:30 — Compensation structures, commissions, and incentivizing performance32:31–35:30 — Sales advice Macy disagrees with and the problem with vague personal branding35:31–37:45 — Messaging clarity, authority, and final takeaways on sustainable sales growthResourcesFollow @millionsweremade on Instagram for frameworks + strategy tipsConnect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored Premier Website: Millions Were MadeConnect with Macy McNeely:Website: http://www.thesalesgirls.comInstagram: @thesalesgirlsofficialYoutube: https://www.youtube.com/@Macy_McNeely“Getting Seriously Good at Selling” Masterclass: https://go.thesalesgirls.com/masterclass-register

In this episode of Millions Were Made, Jessica Marx and Brooke Dumas break down one of the most important skills founders must develop: knowing when to take business advice—and when not to.With endless podcasts, masterminds, social media content, and business opinions available today, many entrepreneurs find themselves overwhelmed by conflicting strategies and constantly chasing solutions that may not actually apply to their business. Jessica explains why generalized advice often leads founders into expensive detours, reactive decision-making, and operational inefficiencies.Together, they discuss the importance of understanding your company’s data, analytics, profitability, customer behavior, and operational structure before implementing new strategies. They also explore why successful founders learn how to think critically about their business instead of blindly copying what worked for someone else.Jessica shares practical insight into scaling responsibly, avoiding common hiring and growth mistakes, using AI strategically, and identifying when expert guidance is actually worth the investment.Together, they discuss:Why generalized business advice often failsThe dangers of “copy-and-paste” entrepreneurshipHow to evaluate whether advice applies to your businessThe importance of data-driven decision-makingWhy founders need to understand their numbers and operationsCommon scaling and hiring mistakesThe difference between thinking strategically vs. “thinking bigger”Practical ways to self-audit your businessSmart ways to use AI without relying on it for strategyWhy targeted expert advice often creates better results than endless mastermindsIf you’ve ever felt overwhelmed by too many opinions, strategies, or business trends, this episode offers a practical framework for making more intentional and strategic decisions as a founder.Listen now to learn how to filter business advice effectively and build a company based on clarity, data, and sustainable growth.Mini-timeline00:00–01:45 — Introduction to information overload and the challenge of navigating business advice01:46–04:20 — Why generalized advice often fails and the importance of business context04:21–07:15 — Understanding data, analytics, and asking better strategic questions07:16–09:20 — Teaching founders how to think critically instead of seeking quick answers09:21–11:55 — High-level decision-making, leverage, and the “fast pass” in business growth11:56–13:55 — The risks of focusing too early on building a “$100 million company”13:56–15:55 — Scaling challenges, hiring mistakes, and operational blind spots15:56–18:20 — How founders can begin self-auditing their business effectively18:21–19:50 — Marketing trends, customer behavior, and repositioning strategies19:51–20:50 — Responsible ways to use AI within business operations20:51–22:25 — Why targeted expert support often outperforms broad business education22:26–End — Final takeaways on discernment, strategic growth, and founder decision-makingResourcesFollow @millionsweremade on Instagram for frameworks + strategy tips2026 Business Planner: https://astounding-founder-8808.kit.com/products/2026-business-planner Listen to the previous Millions Were Made episode on AI Strategy: Episode 73Connect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored Premier Website: Millions Were Made

In this episode of Millions Were Made, Jessica Marx and Brooke Dumas explore a critical shift impacting nearly every business today: evolving buyer psychology.While many founders continue to operate using strategies that were effective in the past, today’s buyers are making decisions differently. This conversation breaks down the key factors behind that shift—from post-2020 economic cycles and inflation to the rise of social media selling and the resulting erosion of trust in the marketplace.Jessica provides a clear and grounded perspective on what has changed and why sales cycles are now longer, more complex, and more relationship-driven. Buyers are no longer making quick, impulse decisions. Instead, they are more cautious, more informed, and more intentional about where they invest their time and money.At the same time, businesses themselves have also evolved—becoming more selective about the clients they work with and placing greater emphasis on alignment, readiness, and long-term fit.Together, they discuss:The economic and behavioral shifts that reshaped buyer decision-makingWhy trust has become one of the most important factors in salesHow the rise of online selling contributed to buyer skepticismThe reality of longer, more deliberate sales cyclesThe importance of lead nurturing and consistent follow-upWhy responsiveness and urgency still play a critical role in conversionHow to approach sales conversations without appearing transactionalCommon gaps in messaging, positioning, and overall sales processWhy “price objections” often reflect deeper value or clarity issuesJessica also shares practical guidance for founders looking to strengthen their sales pipeline—from improving internal processes to focusing on delivering measurable results and building long-term relationships.If you’ve noticed changes in how your audience engages, evaluates, or invests, this episode offers both clarity and direction on how to adapt.Listen now to better understand today’s buyer—and how to position your business for sustainable growth.Mini-timeline00:00–02:30 — Introduction and overview of changing buyer behavior 02:31–06:30 — Economic shifts since 2020 and their impact on spending patterns 06:31–10:00 — Inflation, social media influence, and the rise of buyer skepticism 10:01–13:30 — Declining trust and the importance of credibility in decision-making 13:31–17:00 — Why sales cycles are becoming longer and more complex 17:01–20:30 — Increased selectivity from both buyers and businesses 20:31–24:30 — Understanding the reality of modern sales processes 24:31–28:30 — The role of consistent follow-up and relationship-building 28:31–32:30 — Nurturing leads throughout the entire customer journey 32:31–35:30 — The importance of responsiveness and operational efficiency 35:31–38:30 — Approaching sales conversations with value and intention 38:31–41:30 — Messaging gaps and what today’s buyers actually respond to 41:31–44:30 — Identifying breakdowns within your sales pipeline 44:31–End — Final insights and actionable takeawaysResourcesFollow @millionsweremade on Instagram for frameworks + strategy tipsConnect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored Premier Website: Millions Were Made

Many founders begin their entrepreneurial journey deeply involved in networking, relationship-building, and strategic visibility. However, as the business grows and operational demands increase, it is common for founders to step back from these activities—often unintentionally. While this shift may feel necessary, it can lead to a gradual decline in sales, reduced market visibility, and a disconnect from evolving industry trends.In this episode of Millions Were Made, Jessica Marx and Brooke Dumas address a critical yet often overlooked factor in sustained business growth: the founder’s role in business development. They explore why business development must remain a consistent priority at every stage of growth. Jessica provides a clear distinction between marketing and business development, emphasizing that while marketing supports visibility, business development drives strategic direction, partnerships, and long-term positioning.Key topics include:• Why stepping away from business development can lead to declining sales and missed opportunities• The distinction between marketing activities and true business development• How founders can remain competitive by staying informed on market trends and industry shifts• Identifying which aspects of business development require direct CEO involvement• Recognizing the signs of a disconnect between the founder and the business• Practical strategies for rebuilding a consistent business development rhythm• How to approach networking and industry conversations with intention and value• Recommended time allocation for business development on a weekly basisIf you are experiencing a slowdown in growth, a lack of clarity in direction, or reduced engagement with your market, this episode provides actionable insights to help you realign and move forward with confidence. Listen now!Mini-timeline00:00–00:50 — Introduction and overview of the episode topic00:51–01:45 — Common founder pattern: early engagement followed by withdrawal from business development01:46–04:45 — The importance of ongoing business development at all growth stages04:46–07:05 — Defining business development and differentiating it from marketing07:06–10:40 — The role of market awareness, technology, and strategic positioning10:41–13:20 — Delegation vs. CEO responsibility in business development13:21–16:30 — Key indicator of misalignment: lack of clarity in business direction16:31–18:50 — Where to begin when pipeline and sales begin to decline18:51–20:20 — Effective networking: maintaining professionalism and strategic intent20:21–21:45 — Establishing a structured and sustainable business development routine21:46–End — Final insights on long-term growth and maintaining founder involvementResourcesFollow @millionsweremade on Instagram for frameworks + strategy tipsConnect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored PremierWebsite: Millions Were Made

In this episode of Millions Were Made, Jessica Marx is joined by Brooke Dumas to continue their onboarding series with a practical, implementation-focused discussion.Following Part 1, this episode outlines the exact 90-day onboarding framework they use with six and seven, and even eight-figure companies to ensure new hires are set up for long-term success. Drawing from their experience working directly inside growing organizations, Jessica and Brooke explain how structured onboarding reduces employee turnover, improves performance, and supports scalable growth.They walk through what effective onboarding looks like across the first 30, 60, and 90 days—emphasizing the importance of clear expectations, documented systems, and a gradual transition from training to execution.In this episode, they covered:Why onboarding should be structured before hiring beginsThe role of SOPs and documentation in employee successWhat to prioritize in the first 30 days of onboardingTransitioning from training to execution in a sustainable wayEstablishing clear communication expectations between founders and team membersThe importance of standardizing processes across roles and departmentsHow explaining the “why” improves employee decision-making and ownershipAligning onboarding systems with your leadership styleIf you are currently hiring or planning to expand your team, implementing a structured onboarding system is essential.So what are you waiting for? Tune in now—and don’t forget to listen to Part 1 so you don’t miss the full framework.Mini-timeline01:04–02:47 — Brooke’s role as a fractional COO and onboarding specialist02:48–05:21 — Common hiring and onboarding challenges in scaling businesses05:22–07:18 — Where to begin when building an onboarding framework07:19–09:20 — The importance of prioritizing learning in the first 30 days09:21–11:10 — Risks of unstructured or “sink-or-swim” onboarding approaches11:11–12:51 — Standardizing processes to maintain consistent client experience12:52–14:11 — Building effective SOPs and internal documentation14:12–15:23 — Structuring the first 30 days with clear daily and weekly guidance15:24–16:52 — Aligning onboarding with business goals and direction16:53–18:57 — Setting communication expectations and reporting cadence18:58–20:29 — Teaching employees to think strategically through context and reasoning20:30–22:36 — Adapting onboarding to your leadership style22:37–24:11 — Balancing accessibility with autonomy24:12–26:56 — Overview of the 90-day onboarding framework and tools26:57–End — Additional resources and implementation supportResources90-Day Onboarding Framework (template and checklist: https://astounding-founder-8808.kit.com/products/onboarding-blueprint Follow @millionsweremade on Instagram for frameworks + strategy tipsConnect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored Premier Website: Millions Were Made

In this episode of Millions Were Made, Jessica Marx is joined by Brooke Dumas, the Fractional COO brand of Tailored Premier, to examine one of the most overlooked drivers of team performance: ONBOARDING.While many founders dedicate significant time and resources to hiring, far fewer implement a structured onboarding process that ensures new team members are set up for success. The result is often misalignment, underperformance, and early turnover—despite hiring highly qualified individuals.Jessica and Brooke introduce their proprietary 90-day onboarding framework, a system implemented across client organizations to reduce owner dependency, improve clarity, and accelerate employee performance. They emphasize that the first 90 days are not only a critical evaluation period for the employee, but also a reflection of the company’s leadership, systems, and operational standards.Through real-world observations, they outline the common mistakes founders make—such as assuming experienced hires require minimal guidance—and explain why clearly documented processes, defined expectations, and consistent feedback are essential to building a high-performing team.This episode covers:Why onboarding is a key determinant of employee success and retentionThe risks of relying on assumptions rather than structured trainingHow lack of clarity leads to inefficiency and increased turnoverThe importance of defining and communicating company standardsWhy SOPs, checklists, and documentation are foundational to scalingHow to structure feedback and milestones within the first 90 daysThe long-term impact of a well-executed onboarding experienceThis episode serves as Part 1 of a two-part series designed to help founders implement a scalable and effective onboarding process that supports both team performance and business growth.Listen now and stay tuned for Part 2, where we will provide a detailed breakdown of the onboarding framework and how to implement it within your organization.Mini-timeline00:14–01:03 — Introduction to the 90-day onboarding framework01:04–02:15 — Why onboarding is critical to employee retention02:16–03:18 — The role of onboarding in shaping company culture03:19–04:53 — The risks of assuming new hires will “figure it out”04:54–06:30 — Common onboarding mistakes made by founders06:31–08:15 — Defining and communicating standards of excellence08:16–10:39 — The importance of SOPs, checklists, and structured plans10:40–11:31 — Hiring under pressure: build first or hire first?11:32–13:57 — The consequences of onboarding without infrastructure13:58–15:20 — The cost of early employee turnover15:21–17:52 — Case example: effective onboarding in practice17:53–19:30 — Building employee engagement and long-term commitment19:31–20:27 — Making informed decisions within the first 90 days20:28–22:42 — Preview of Part 2 and framework overviewResources90-Day Onboarding Framework (Download): https://astounding-founder-8808.kit.com/products/onboarding-blueprintFollow @millionsweremade on Instagram for frameworks + strategy tipsConnect with Jessica:Instagram: @millionsweremade | @thejessicamarxWork with Jessica: Tailored PremierWebsite: Millions Were Made