What does it really take to evolve from COO to CEO? Or from startup founder to strategic enterprise leader?

In this episode of Startup Scaleup People, we sit down with Simon Stibbs, an executive coach who has advised 1,000+ CEOs and coached over 30 leaders into top roles across Australia and beyond.

From working with first-time founders to enterprise CEOs managing thousands, Simon reveals the real inner work required to shift mindsets, lead boards, navigate politics, and position yourself for the next big leap.Hosted by Mario Rivas and Tiffany Chown.

📢 About Startup Scaleup PeopleReal stories from startup, scaleup & enterprise leaders. From boardrooms to founder garages — we bring you insights on growth, leadership, funding, exits, and everything in between.New episodes every Sunday at 4PM UK time.

🧭 Chapters

00:00 Welcome & Intro

01:50 Why Simon coaches COOs into CEOs

06:00 Top barriers that block CEO transitions

09:20 Coaching women to reframe their strategic value

13:10 What young CEOs need to focus on

16:30 Managing boards and internal politics

24:30 Leading teams across 14 countries

30:00 Building the right network for CEO transitions

💬 Key Highlights▸

Why COO-to-CEO is one of the hardest transitions

▸ The key blind spots even high-performing leaders face

▸ How language, perception & framing shape career growth

▸ What separates a strategist from a "troubleshooter"

▸ Why board relationships can make or break your influence

▸ Lessons from working with CEOs managing 15,000+ people ▸ The importance of developing a board portfolio early

👥 Who Should ListenAspiring CEOs • COOs & C-suite leaders • First-time founders • Board advisors • Leadership coaches • Investors & executive recruiters

🔗 Follow & SubscribeInstagram: https://www.instagram.com/startupscaleuppeople/TikTok: https://www.tiktok.com/@square.circle.podcastSpotify: https://open.spotify.com/show/3804Om0XrGG1gNRsev6DlUApple Podcasts: https://podcasts.apple.com/gb/podcast/startup-scaleup-people/id1847157416LinkedIn (Page): https://www.linkedin.com/company/squarecirclecommunity/LinkedIn (Mario): https://www.linkedin.com/in/mariorivassanchez/Community Website: https://www.squarecircle.me

🧠 Keywords

startup, scaleup, entrepreneurship, business podcast, leadership, business growth, founder mindset, startup stories, scaleup journey, entrepreneur advice, business strategy, innovation, venture capital, startup founders, startup funding, executive leadership, enterprise leadership, enterprise strategy, business transformation, board of directors, fractional leadership, NEDs, startup scaleup people, coaching, board politics, COO to CEO, career growth, high-performance leadership

#startupleadership #businessgrowth #scaleups #enterprise #boardleadership #venturecapital #startup #founderstories #innovation #businesspodcast #careergrowth #operationalexcellence #leadershipdevelopment #startupstrategy #funding #exitstrategies #teambuilding #corporategovernance #techfounders #startupscaleuppeople #startupfunding #vc #podcast #shorts #leadership #entrepreneurship #investing #governance #peoplestories #experience #leadershipskills #leadershiplessons #businessleadership #businessstrategy #businessideas #businesssuccessstories #businesssuccess #biotech #saas #failure #fail #entrepreneur #howtoinvest #hiring #digitaltransformation #expansion #businessexpansion #technology #successmindset #motivation #mindset #perseverance #resilience #Emprendimiento #Empreendedorismo #Entrepreneuriat #Unternehmertum #Imprenditorialità #Ondernemerschap #उद्यमिता #ريادة_الأعمال #Girişimcilik #Kewirausahaan #Pagnenegosyo #创业 #起業家精神 #기업가정심

From scaling SaaS to multiple private equity exits and now building AI-powered cybersecurity, David Rajakovich shares what it takes to lead, exit, and build again.This episode features his journey from the US Army to leading Acuity Risk Management and Skill Dynamics, scaling ARR past $10M and navigating two major exits before launching a new AI platform tackling enterprise threat intelligence.

🎧 Hosted by Mario Rivas and Tiffany Chown

📢 About Startup Scaleup PeopleReal stories from startup, scaleup & enterprise leaders. From boardrooms to founder garages — we bring you insights on growth, leadership, funding, exits, and everything in between.New episodes every Sunday at 4PM UK time.

🧭 Chapters

00:00 Intro & Army to SaaS

04:12 Scaling Skill Dynamics

09:03 Private Equity Exit Lessons

13:20 Building Acuity Risk Management

17:55 Identifying Big Cyber Threats

22:10 Launching New AI Venture

26:30 Founders vs. Risk Tolerance

30:00 Advice on Exits & Leadership

💬 Key Highlights▸ Led ARR from $1M to $10M+▸ Built and sold two companies to PE firms▸ New startup using AI to predict cyber threats▸ Lessons on board governance and risk▸ Balancing resilience and fast decision-making

👥 Who Should ListenCybersecurity leaders • SaaS founders • PE-backed execs • Risk & compliance professionals • Tech investors🔗 Follow & SubscribeInstagram: https://www.instagram.com/startupscaleuppeople/TikTok: https://www.tiktok.com/@square.circle.podcastSpotify: https://open.spotify.com/show/3804Om0XrGG1gNRsev6DlUApple Podcasts: https://podcasts.apple.com/gb/podcast/startup-scaleup-people/id1847157416LinkedIn Page: https://www.linkedin.com/company/squarecirclecommunity/Mario Rivas: https://www.linkedin.com/in/mariorivassanchez/Community: https://www.squarecircle.me

🧠 Keywords

startup, scaleup, entrepreneurship, business podcast, leadership, business growth, founder mindset, startup stories, scaleup journey, entrepreneur advice, business strategy, innovation, venture capital, startup founders, startup funding, executive leadership, enterprise leadership, enterprise strategy, business transformation, board of directors, fractional leadership, NEDs, startup scaleup people, cybersecurity, SaaS, private equity, ARR, exits, threat intelligence, AI platform

#startupleadership #businessgrowth #scaleups #enterprise #boardleadership #venturecapital #startup #founderstories #innovation #businesspodcast #careergrowth #operationalexcellence #leadershipdevelopment #startupstrategy #funding #exitstrategies #teambuilding #corporategovernance #techfounders #startupscaleuppeople #startupfunding #vc #podcast #shorts #leadership #fintech #entrepreneurship #investing #governance #peoplestories #experience #leadershipskills #leadershiplessons #businessleadership #businessstrategy #businessideas #businesssuccessstories #businesssuccess #biotech #saas #failure #fail #entrepreneur #howtoinvest #hiring #digitaltransformation #expansion #businessexpansion #energy #technology #techstartup #techfounders #successmindset #motivation #mindset #perseverance #resilience #Emprendimiento #Empreendedorismo #Entrepreneuriat #Unternehmertum #Imprenditorialità #Ondernemerschap #उद्यमिता #ريادة_الأعمال #Girişimcilik #Kewirausahaan #Pagnenegosyo #创业 #起業家精神 #기업가정신

Can idle savings be reimagined as a global growth engine?

In this episode of Startup Scaleup People, we speak with Mike Saraswat, co-founder and CEO of Stoa, a fintech platform unlocking trillions in idle cash and turning it into lifestyle perks, SaaS credits, and value for consumers and businesses.

🎧 Hosted by Mario Rivas and Tiffany Shown, this episode explores saving behavior, global cash inertia, regulatory pivots, the US vs UK fundraising mindsets, and Mike’s journey from ad agency founder to mission-driven fintech disruptor.

📢 About Startup Scaleup PeopleReal stories from startup, scaleup & enterprise leaders. From boardrooms to founder garages — we bring you insights on growth, leadership, funding, exits, and everything in between.

New episodes every Sunday at 4PM UK time.

🧭 Chapters

00:00 Intro to Mike Saraswat and the Idle Cash Problem

03:00 From Blockchain to Fintech: Pivoting Beyond Regulation

07:00 The $600B+ Opportunity in UK Idle Cash Alone

10:00 Building Stoa Pots: Get Netflix, SaaS & Perks Instead of Interest

14:00 Going Global: Expansion in the US and B2B Strategy

18:00 Fundraising Realities: UK vs US Investors

23:00 Lessons in Setbacks, Startups & Human Behavior

27:00 What Makes an Idea “Big Enough” to Scare You (and Investors)

💬 Key Highlights

▸ $600B+ in UK household idle cash, $50T+ globally

▸ Pivoted from blockchain + stablecoins to regulated savings

▸ Users “park” up to £1M and get lifestyle perks like Netflix, Strava, Coachella

▸ New B2B features for SMBs to optimize unused cash

▸ 5-7 minute full KYC/onboarding using Griffin + Yappily

👥 Who Should ListenFintech founders • Wealth managers • Banking execs • Investors • SaaS product teams • Consumer behavior researchers

🔗 Follow & Subscribe

📌 https://www.instagram.com/startupscaleuppeople/

📌 https://www.tiktok.com/@square.circle.podcast

📌 https://open.spotify.com/show/3804Om0XrGG1gNRsev6DlU

📌 https://podcasts.apple.com/gb/podcast/startup-scaleup-people/id1847157416

📌 https://www.linkedin.com/company/squarecirclecommunity/📌 https://www.linkedin.com/in/mariorivassanchez/

📌 https://www.squarecircle.me

🧠 Keywords

startup, scaleup, entrepreneurship, business podcast, leadership, business growth, founder mindset, startup stories, scaleup journey, entrepreneur advice, business strategy, innovation, venture capital, startup founders, startup funding, executive leadership, enterprise leadership, enterprise strategy, business transformation, board of directors, fractional leadership, NEDs, startup scaleup people, fintech, savings, deposits, perks, idle cash, SMB finance

#startupleadership #businessgrowth #scaleups #enterprise #boardleadership #venturecapital #startup #founderstories #innovation #businesspodcast #careergrowth #operationalexcellence #leadershipdevelopment #startupstrategy #funding #exitstrategies #teambuilding #corporategovernance #techfounders #startupscaleuppeople #startupfunding #vc #podcast #shorts #leadership #fintech #entrepreneurship #investing #governance #peoplestories #experience #leadershipskills #leadershiplessons #businessleadership #businessstrategy #businessideas #businesssuccessstories #businesssuccess #biotech #saas #failure #fail #entrepreneur #howtoinvest #hiring #digitaltransformation #expansion #businessexpansion #energy #technology #techstartup #techfounders #successmindset #motivation #mindset #perseverance #resilience #Emprendimiento #Empreendedorismo #Entrepreneuriat #Unternehmertum #Imprenditorialità #Ondernemerschap #उद्यमिता #ريادة_الأعمال #Girişimcilik #Kewirausahaan #Pagnenegosyo #创业 #起業家精神 #기업가정신

Can AI and WhatsApp save lives by helping people actually show up for care?In this episode of Startup Scaleup People, we speak with Neill Dunwoody, COO & Co-Founder of SPRYT, a healthtech startup that helps health systems reduce missed appointments and increase cancer screenings through conversational AI.

🎧 Hosted by Mario Rivas, this episode goes deep on AI healthcare orchestration, no-show prediction, regulatory barriers, health tech scaling, and building a high-trust, award-winning startup across the UK, Ireland, and now the US.

📢 About Startup Scaleup PeopleReal stories from startup, scaleup & enterprise leaders. From boardrooms to founder garages — we bring you insights on growth, leadership, funding, exits, and everything in between.New episodes every Sunday at 4PM UK time.

🧭 Chapters

00:00 Intro to SPRYT and Healthcare Problem

03:00 NHS Success: Cervical Screening +160%

06:30 Pivot from Sports App to MedTech Innovation

10:00 Building a Global Health Orchestration Platform

15:00 Cancer Prevention, HPV & Vaccine Education

20:00 U.S. Expansion, Mayo Clinic & New Partnerships

25:00 Scaling Leadership and Strategic Growth

30:00 Hard Lessons in Healthtech, Funding & Mission-Driven Work

💬 Key Highlights

▸ AI + WhatsApp engagement boosted cancer screening rates by 160%

▸ First company to deploy conversational AI in UK’s NHS

▸ Saved 8+ admin hours/week and 30%+ in SMS costs

▸ Strategic partnerships with MediDrive & Mayo Clinic Accelerate

▸ Vision: 50B+ patient engagements/year by 2035, global health orchestration

👥 Who Should ListenHealthtech founders

• NHS innovators

• AI ops teams

• US payers & providers

• Seed-stage operators

• Cancer & screening advocates

🔗 Follow & Subscribe

📌 https://www.instagram.com/startupscaleuppeople/

📌 https://www.tiktok.com/@square.circle.podcast

📌 https://open.spotify.com/show/3804Om0XrGG1gNRsev6DlU📌 https://podcasts.apple.com/gb/podcast/startup-scaleup-people/id1847157416

📌 https://www.linkedin.com/company/squarecirclecommunity/📌 https://www.linkedin.com/in/mariorivassanchez/

📌 https://www.squarecircle.me

🧠 Keywords

startup, scaleup, entrepreneurship, business podcast, leadership, business growth, founder mindset, startup stories, scaleup journey, entrepreneur advice, business strategy, innovation, venture capital, startup founders, startup funding, executive leadership, enterprise leadership, enterprise strategy, business transformation, board of directors, fractional leadership, NEDs, startup scaleup people, healthtech, cancer screening, NHS innovation, AI orchestration, WhatsApp AI

#startupleadership #businessgrowth #scaleups #enterprise #boardleadership #venturecapital #startup #founderstories #innovation #businesspodcast #careergrowth #operationalexcellence #leadershipdevelopment #startupstrategy #funding #exitstrategies #teambuilding #corporategovernance #techfounders #startupscaleuppeople #startupfunding #vc #podcast #shorts #leadership #fintech #entrepreneurship #investing #governance #peoplestories #experience #leadershipskills #leadershiplessons #businessleadership #businessstrategy #businessideas #businesssuccessstories #businesssuccess #biotech #saas #failure #fail #entrepreneur #howtoinvest #hiring #digitaltransformation #expansion #businessexpansion #energy #technology #techstartup #techfounders #successmindset #motivation #mindset #perseverance #resilience #Emprendimiento #Empreendedorismo #Entrepreneuriat #Unternehmertum #Imprenditorialità #Ondernemerschap #उद्यमिता #ريادة_الأعمال #Girişimcilik #Kewirausahaan #Pagnenegosyo #创业 #起業家精神 #기업가정신

From mission-critical systems at Ford to scaling AI-powered identity verification at Onfido, Lyubomira Dimitrova has helped lead one of Europe’s largest tech exits.

In this episode of Startup Scaleup People, we speak with Lyubomira Dimitrova, co-founder, fractional CPTO, and former SVP of Engineering at Onfido, a RegTech company acquired for $650M.

She reflects on her transition from enterprise to startup, scaling a team through hypergrowth, and building a new AI venture.

🎧 Hosted by Mario Rivas and Tiffany Shown, this episode explores building psychological safety, technical debt, scaling leadership, and why not all models (like the Spotify one) fit every company.

📢 About Startup Scaleup PeopleReal stories from startup, scaleup & enterprise leaders. From boardrooms to founder garages — we bring you insights on growth, leadership, funding, exits, and everything in between.New episodes every Sunday at 4PM UK time.

🧭 Chapters

00:00 From Ford to Founders: Lyubomira’s Global Journey

03:50 Lessons from Mission-Critical Enterprise IT

06:30 Joining Onfido: From Process Gaps to Hypergrowth

11:00 Scaling to $100M ARR and a $650M Exit

15:00 Technical Debt, Product Risk & Communication2

0:00 Building AI Ops & Cross-Functional Teams

25:00 Psychological Safety vs. Pressure to Perform

30:00 CTO + CPO Roles & Starting a New AI Venture

💬 Key Highlights

▸ Led Onfido’s technical teams through $100M+ ARR & $650M acquisition

▸ Former enterprise leader at Ford, now co-founder in RegTech AI

▸ Expert in scaling systems, eliminating tech debt & aligning GTM

▸ Advocates for women in leadership and product-tech hybrids

▸ Now building again in stealth-mode with focus on financial services

👥 Who Should ListenTech founders • Enterprise engineers • Product/Eng leaders • RegTech and AI builders • Fractional CPTOs • Women in Tech

🔗 Follow & Subscribe

📌 https://www.instagram.com/startupscaleuppeople/

📌 https://www.tiktok.com/@square.circle.podcast📌 https://open.spotify.com/show/3804Om0XrGG1gNRsev6DlU📌 https://podcasts.apple.com/gb/podcast/startup-scaleup-people/id1847157416📌 https://www.linkedin.com/company/squarecirclecommunity/📌 https://www.linkedin.com/in/mariorivassanchez/📌 https://www.squarecircle.me

🧠 Keywordsstartup, scaleup, entrepreneurship, business podcast, leadership, business growth, founder mindset, startup stories, scaleup journey, entrepreneur advice, business strategy, innovation, venture capital, startup founders, startup funding, executive leadership, enterprise leadership, enterprise strategy, business transformation, board of directors, fractional leadership, NEDs, startup scaleup people, fintech, RegTech, AI, CPTO, product strategy, women in tech

#startupleadership #businessgrowth #scaleups #enterprise #boardleadership #venturecapital #startup #founderstories #innovation #businesspodcast #careergrowth #operationalexcellence #leadershipdevelopment #startupstrategy #funding #exitstrategies #teambuilding #corporategovernance #techfounders #startupscaleuppeople #startupfunding #vc #podcast #shorts #leadership #fintech #entrepreneurship #investing #governance #peoplestories #experience #leadershipskills #leadershiplessons #businessleadership #businessstrategy #businessideas #businesssuccessstories #businesssuccess #biotech #saas #failure #fail #entrepreneur #howtoinvest #hiring #digitaltransformation #expansion #businessexpansion #energy #technology #techstartup #techfounders #successmindset #motivation #mindset #perseverance #resilience #Emprendimiento #Empreendedorismo #Entrepreneuriat #Unternehmertum #Imprenditorialità #Ondernemerschap #उद्यमिता #ريادة_الأعمال #Girişimcilik #Kewirausahaan #Pagnenegosyo #创业 #起業家精神 #기업가정신

From COO of PolyAI to investor at Point72, Yan Zhang reveals what it really takes to scale AI startups globally — and why he’s building again.

In this episode of Startup Scaleup People, we sit down with Yan Zhang, former Chief Operating Officer at PolyAI, now an angel investor, mentor at Cambridge Founders and Deep Tech Labs, and Principal at Point72 Ventures.

Yan unpacks how PolyAI scaled voice AI across 20+ countries and how he now supports founders with funding and operational insight.

🎧 Hosted by Mario Rivas this conversation explores scaling enterprise AI, operating under constraints, go-to-market in the U.S. vs Europe, sales hiring, founder resilience, and why Yan still wants to build.

📢 About Startup Scaleup People
Real stories from startup, scaleup, and enterprise leaders. From boardrooms to founder garages — we bring you insights on growth, leadership, funding, exits, and everything in between.
New episodes every Sunday at 4PM UK time.

🧭 Chapters
00:00 Yan’s Global Career Journey
04:00 Corporate Development, Random House & China Expansion
08:00 Joining PolyAI & Focus on Voice Modality
11:00 Understanding Constraints and Business Strategy
15:00 Scaling to $50M ARR & Global Teams
20:00 Sales Hiring Challenges & Expansion into the U.S.
24:00 From Operator to Investor: 400+ AI Startups Reviewed
28:00 What He’ll Build Next & Advice for Founders

💬 Key Highlights
▸ COO at PolyAI: Scaled enterprise AI voice to $50M revenue
▸ Led expansion into 20+ countries and U.S. GTM
▸ Principal at Point72 Ventures, investing in applied AI startups
▸ 15+ angel investments across Europe & Silicon Valley
▸ Mentor at Cambridge Founders & Deep Tech Labs
▸ Practical insights on sales hiring, constraints, resilience, and exits

👥 Who Should Listen
AI founders, B2B operators, enterprise sales leaders, investors, and founders scaling internationally.

🔗 Follow & Subscribe
Instagram: https://www.instagram.com/startupscaleuppeople/
TikTok: https://www.tiktok.com/@square.circle.podcast
Spotify: https://open.spotify.com/show/3804Om0XrGG1gNRsev6DlU
Apple Podcasts: https://podcasts.apple.com/gb/podcast/startup-scaleup-people/id1847157416
LinkedIn (Community): https://www.linkedin.com/company/squarecirclecommunity/
LinkedIn (Host): https://www.linkedin.com/in/mariorivassanchez/
Website: https://www.squarecircle.me

🏷️
startupleadership, businessgrowth, scaleups, enterprise, venturecapital, startup, founderstories, innovation, businesspodcast, leadership, startupstrategy, funding, exits, techfounders, saas, ai, investing, resilience

How do you lead product through hypergrowth, scale to IPO, and now advise the next generation of startups? In this episode of Startup Scaleup People, we sit down with Adriana Landaverde, a seasoned Chief Product Officer with 3 successful exits, including Trulia (IPO) and Nutmeg (acquired by JPMorgan).

From El Salvador to Silicon Valley to London, Adriana shares what it takes to scale product teams, build retention strategies, and become a trusted advisor to early-stage founders.

📢 About Startup Scaleup People: Real stories from startup, scaleup & enterprise leaders. From boardrooms to founder garages — we bring you insights on growth, leadership, funding, exits, and everything in between.New episodes every Sunday at 4PM UK time.

🧭 Chapters

00:00 Intro & Adriana's Background

02:00 What IPO Teaches You That Books Don’t

07:00 From El Salvador to Stanford to Silicon Valley

10:30 Trulia, Nutmeg & Product Leadership Across Stages

14:00 Balancing Customer Needs with Strategy

17:00 Aligning Sales, Product & Go-To-Market Teams

22:00 Nutmeg Launch Failure: Lessons in Execution

26:00 What Makes a Good Founder-Advisor Fit?

33:00 Clarity, Team Roles & Strategy for Scaling Startups

💬 Key Highlights

▸ Led product at Trulia (IPO $450M+), Nutmeg (acquired by JPMorgan), JamesEdition and more

▸ Scaled B2B & B2C product orgs across UK, US & EU

▸ Deep insights on retention, churn, and cross-functional product teams

▸ Advisor to Series A/B startups as fractional CPO

▸ Built product strategy with customer empathy + commercial focus

▸ Evangelist for sales + product collaboration

👥 Who Should Listen

Product leaders • Founders • CPOs • B2B/B2C Operators • Fractionals • Investors • Go-to-market teams

🔗 Follow & Subscribe

📌 https://www.instagram.com/startupscaleuppeople/

📌 https://www.tiktok.com/@square.circle.podcast

📌 https://open.spotify.com/show/3804Om0XrGG1gNRsev6DlU

📌 https://podcasts.apple.com/gb/podcast/startup-scaleup-people/id1847157416

📌 https://www.linkedin.com/company/squarecirclecommunity/📌

https://www.linkedin.com/in/mariorivassanchez/

📌 https://www.squarecircle.me

🧠 Keywordsstartup, scaleup, entrepreneurship, business podcast, leadership, business growth, founder mindset, startup stories, scaleup journey, entrepreneur advice, business strategy, innovation, venture capital, startup founders, startup funding, executive leadership, enterprise strategy, enterprise leadership, business transformation, board of directors, fractional leadership, NEDs, startup scaleup people, fintech, product leadership, retention, advisor

#startupleadership #businessgrowth #scaleups #enterprise #boardleadership #venturecapital #startup #founderstories #innovation #businesspodcast #careergrowth #operationalexcellence #leadershipdevelopment #startupstrategy #funding #exitstrategies #teambuilding #corporategovernance #techfounders #startupscaleuppeople #startupfunding #vc #podcast #shorts #leadership #fintech #entrepreneurship #investing #governance #peoplestories #experience #leadershipskills #leadershiplessons #businessleadership #businessstrategy #businessideas #businesssuccessstories #businesssuccess #biotech #saas #failure #fail #entrepreneur #howtoinvest #hiring #digitaltransformation #expansion #businessexpansion #energy #technology #techstartup #techfounders #successmindset #motivation #mindset #perseverance #resilience #Emprendimiento #Empreendedorismo #Entrepreneuriat #Unternehmertum #Imprenditorialità #Ondernemerschap #उद्यमिता #ريادة_الأعمال #Girişimcilik #Kewirausahaan #Pagnenegosyo #创业 #起業家精神 #기업가정신

How do you build a global, high-impact healthtech business bootstrapped and profitable from day one?

In this episode of Startup Scaleup People, we speak with Jonathan Larbey, CEO & Founder of T-Pro, an AI-powered clinical documentation platform trusted by over 130,000 clinicians globally.

🎧 Hosted by Mario Rivas this conversation dives into building a healthcare SaaS business from zero to $30M ARR through acquisitions, product innovation, global expansion, and governance.

Real stories from startup, scaleup & enterprise leaders. From boardrooms to founder garages — we bring you insights on growth, leadership, funding, exits, and everything in between.

New episodes every Sunday at 4PM UK time.

🧭 Chapters

00:00 Jonathan’s Journey: From Rugby to Tech CEO
04:00 Solving Clinical Documentation at Scale
08:00 Global Expansion: UK, ANZ, India & More
12:00 Impact on Clinicians & Healthcare Systems
17:00 Reaching $30M ARR with Strategic Acquisitions
23:00 Governance, Boards & Private Equity Partners
29:00 Lessons in Due Diligence & Integration
36:00 Founder Advice & Leadership Lessons

💬 Key Highlights

▸ 130K+ active users, tens of millions of documents processed annually
▸ Bootstrapped and profitable from the start — now private equity-backed
▸ Strategic acquisitions in Ireland, UK, Australia, India & New Zealand
▸ Built M&A playbook and acquisition runway for future growth
▸ Solving clinician burnout & documentation inefficiencies with AI
▸ Active board with PE firm Livingbridge and top-tier chair
▸ Insights on scaling in highly regulated global markets

👥 Who Should Listen

Healthtech founders • SaaS leaders • PE-backed executives • Board directors • Clinicians • Global operators • Investors

🔗 Follow & Subscribe

📌 https://www.instagram.com/startupscaleuppeople/
📌 https://www.tiktok.com/@square.circle.podcast
📌 https://open.spotify.com/show/3804Om0XrGG1gNRsev6DlU
📌 https://podcasts.apple.com/gb/podcast/startup-scaleup-people/id1847157416
📌 https://www.linkedin.com/company/squarecirclecommunity/
📌 https://www.linkedin.com/in/mariorivassanchez/
📌 https://www.squarecircle.me

🧠 Keywords

startup, scaleup, entrepreneurship, business podcast, leadership, business growth, founder mindset, startup stories, scaleup journey, entrepreneur advice, business strategy, innovation, venture capital, startup founders, startup funding, executive leadership, enterprise leadership, enterprise strategy, business transformation, board of directors, fractional leadership, NEDs, startup scaleup people, AI, healthtech, SaaS, M&A, private equity, clinician productivity

#startupleadership #businessgrowth #scaleups #enterprise #boardleadership #venturecapital #startup #founderstories #innovation #businesspodcast #careergrowth #operationalexcellence #leadershipdevelopment #startupstrategy #funding #exitstrategies #teambuilding #corporategovernance #techfounders #startupscaleuppeople #startupfunding #vc #podcast #shorts #leadership #fintech #entrepreneurship #investing #governance #peoplestories #experience #leadershipskills #leadershiplessons #businessleadership #businessstrategy #businessideas #businesssuccessstories #businesssuccess #biotech #saas #failure #fail #entrepreneur #howtoinvest #hiring #digitaltransformation #expansion #businessexpansion #energy #technology #techstartup #techfounders #successmindset #motivation #mindset #perseverance #resilience #Emprendimiento #Empreendedorismo #Entrepreneuriat #Unternehmertum #Imprenditorialità #Ondernemerschap #उद्यमिता #ريادة_الأعمال #Girişimcilik #Kewirausahaan #Pagnenegosyo #创业 #起業家精神 #기업가정신