Success Leaves Clues with Robin Bailey and Al McDonald

What happens when an investor sees an overlooked healthcare need and decides to build a business around it?In this episode of Success Leaves Clues, Robin Bailey and guest co-host Kim Seipt sit down with Lindsay Jephcott, Co-Founder of Lume Women + Health, to explore the women’s health gap and the entrepreneurial journey behind a company working to address it.Lindsay explains how her background as an investment executive helped her recognize an underserved market in women’s midlife health. Together with three physician co-founders, she set out to create a menopause clinic despite warnings that women would not want to talk about aging. As the team listened to patients, that initial concept evolved into a broader executive medical offering focused on women’s preventive care and healthy aging.She shares why menopause deserves attention from employers, how greater visibility is helping change the conversation, and why women should feel empowered to seek answers about their health. The discussion explores Lume’s approach to connecting different areas of care rather than treating each concern in isolation.Lindsay also opens up about the realities of building a company from scratch: navigating rejection, checking your ego, choosing complementary partners, and learning when to act quickly versus when to pause. With a team of 30 at the time of recording, she reflects on how founders’ responsibilities change as a business grows. The conversation closes with her ambitions for physician education, research, advocacy, and a future where the next generation of women can find the care and answers they need.You’ll hear about:How Lindsay’s investment background led her into women’s healthcareWhy the women’s health gap represents an overlooked business opportunityHow menopause became a bigger conversation in workplaces and public lifeWhy Lume evolved from a menopause clinic into broader preventive careHow listening to patients helped shape the company’s directionWhat founders should discuss before entering a business partnershipWhy resilience, humility, and thoughtful decision-making matter when building a companyHow Lindsay hopes to create lasting change through education, research, and accessWe talk about:00:00 Meet Lindsay Jephcott of Lume Women + Health 02:18 Recognizing the women’s health gap through an investor’s lens 08:03 Investment and innovation in women’s healthcare 08:42 Why the conversation about menopause is changing 12:22 Women’s midlife health and a more connected approach to care 18:41 Choosing business partners and sharing leadership 21:17 Building founder resilience and responding to patient needs 23:32 Growing a team of 30 and delegating responsibilities 24:51 Making thoughtful decisions and navigating a career transition 30:56 Creating a legacy through education, research, and accessConnect with LindsayLinkedIn: https://www.linkedin.com/in/lindsay-stollery-jephcott/ Website: https://www.lumewomenshealth.com/team/lindsay-stollery-jephcott  Connect with UsLinkedIn: Robin Bailey and Kim Seipt  Website: Aria Benefits and Caledon Hills Private Wealth

What does a people-first culture look like beyond the words on a company website?In this episode of Success Leaves Clues, Robin Bailey sits down with Sarah Pazzano, Director of People at Jarvis Consulting Group, to explore how leaders can build a workplace where employees feel safe, supported, and able to grow.Sarah explains that a people-first culture requires investment in employee development, psychological safety, and leadership grounded in transparency and empathy. She shares how employee engagement surveys, participation levels, and voluntary turnover can help reveal whether those values are showing up in everyday work. One warning sign leaders may overlook: employees who stop raising concerns.Her perspective comes from a career that began in pharmaceutical packaging operations, moved into the startup world, and led to a deliberate investment in HR education. Sarah also reflects on two years working remotely from Paris and how that experience reshaped her thinking about flexibility, connection, and work-life balance.The conversation closes with Jarvis’s mission to equalize opportunity and maximize potential. Sarah explains why hiring primarily from resumes can overlook newcomers, recent graduates, and people returning after a career break, and why curiosity, learning, and thoughtful questions deserve a closer look.You’ll hear about:How Sarah found her path from pharmaceutical packaging to people operationsWhy authentic networking can open the door to a career changeHow HR education and hands-on experience complement each otherWhat a people-first culture requires in everyday practiceWhy employee silence and low survey participation deserve attentionHow HR and managers can build psychological safety in hybrid teamsWhat working remotely from Paris taught Sarah about work-life balanceHow hiring for potential can uncover talent a resume overlooksWe talk about:00:00 Meet Sarah Pazzano of Jarvis Consulting Group 01:03 From pharmaceutical packaging to startup people operations 03:53 Networking advice for a career change 06:02 Pursuing HR education and finding meaningful work 10:16 HR designations versus hands-on experience 13:12 What a people-first culture actually looks like 16:37 Building psychological safety in hybrid teams 19:21 Working remotely from Paris and rethinking work-life balance 24:37 Hiring for potential beyond resumes and credentials 29:52 Creating pathways for Canada’s overlooked talentConnect with SarahLinkedIn: https://www.linkedin.com/in/sarahpazzano/Company LinkedIn: https://www.linkedin.com/company/jarvisconsulting/Website: https://www.jrvs.ca/  Connect with UsLinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What does it take to turn a homemade snack into a brand stocked by more than 11,000 retailers?In this episode of Success Leaves Clues, Robin Bailey and guest co-host Christine Vigna sit down with Jake Karls, co-founder and rainmaker of Mid-Day Squares. Jake launched the company in 2018 with his sister Leslie and brother-in-law Nick, making bars in a Montreal condo kitchen and delivering orders themselves.Jake shares how inviting customers behind the scenes helped the founders build a community around the brand. He recalls an early turning point when Mid-Day Squares reached its first-year sales goal of $250,000 in just three months. Today, he says the company’s Montreal facility produces roughly 170,000 to 175,000 bars a day.The conversation explores why Jake stepped down as CMO after realizing management was not his strength. As Mid-Day Squares’ rainmaker, he now focuses on storytelling and building relationships that can lead to retail, investment, hiring, and other opportunities over time.Jake also speaks candidly about the burnout that forced him to reconsider his pace. He explains why rest is now part of how he sustains his work, and how regular therapy sessions help the three founders navigate difficult decisions while protecting their relationship as family.You’ll hear about:How Mid-Day Squares grew from hand-delivered samples to thousands of retail locations Why the founders chose to share the difficult parts of building the company What a personal response to a customer problem can mean for a brand Why Jake stepped away from the CMO role and became the company’s rainmaker How long-term relationships have helped Mid-Day Squares find partners and investors What burnout changed about Jake’s approach to work and rest How the founders use regular therapy sessions to communicate through conflict Why Jake wants the next generation to feel confident sharing their own storiesWe talk about:00:00 Christine’s customer experience and Jake’s personal response 04:31 The early days of Mid-Day Squares in a Montreal condo 09:00 The founders’ belief in the business and an early sales milestone 11:47 Why the company shares its entrepreneurial journey openly 12:18 Jake’s experience with burnout and the lesson he learned about rest 21:35 Why Jake moved from CMO to the rainmaker role 23:07 Building friendships and business relationships over time 29:16 Working with family and addressing conflict 30:07 Why the founders committed to regular therapy sessions 38:14 The legacy Jake hopes to leave through Mid-Day SquaresConnect with JakeLinkedIn: https://www.linkedin.com/in/jake-karls-653106ba/ Personal Instagram: https://www.instagram.com/jakekarls_ Instagram: https://www.instagram.com/middaysquare Facebook: https://www.facebook.com/MidDaySquares Website: https://www.middaysquares.com/  Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What separates marketing that looks impressive from marketing that creates measurable business growth?In this episode of Success Leaves Clues, Robin and Al sit down with Alison Simpson, recently retired President and CEO of the Canadian Marketing Association, to explore marketing leadership, brand and culture alignment, business transformation, career growth, and the courage to act before certainty arrives.Alison explains why marketing leaders must speak the language of revenue, profit, customer lifetime value, and market share if they want to influence business strategy. She shares how a customer growth strategy at Holt Renfrew contributed to a 21% annual sales increase and attracted 270,000 loyalty program members in its first year.The conversation also explores the subtle language that reveals when employees no longer feel connected to a brand, why leaders build trust by taking responsibility when something fails, and how accountability can strengthen psychological safety throughout an organization.Drawing on a career that has spanned agency leadership, iconic brands, startups, corporate marketing, and the Canadian Marketing Association, Alison shares the principles that shaped her success: say yes when you are 70% ready, choose clarity over certainty, build relationships before you need them, and treat your career as a landscape rather than a ladder.She also reveals what completing 65 marathons and ultramarathons taught her about preparation, resilience, ego, and the essential difference between something that is hard and something that is harmful.You’ll hear about:How employee language reveals a growing divide between brand and culture Why customer-facing employees are critical to delivering a brand promise How leaders build trust by publicly taking responsibility for mistakes Why marketing needs more than a symbolic seat at the leadership table How to translate marketing activity into measurable business outcomes The strategy that helped generate a 21% annual sales increase at Holt Renfrew Why 70% certainty can become a competitive advantage How to distinguish relationship-building from collecting contacts What endurance racing teaches leaders about preparation and resilience Why ambition, kindness, and integrity are not competing priorities How Alison became the first female CEO in the CMA’s history Why the strongest careers are landscapes rather than laddersWe talk about:00:00 Al’s Great Cycle Challenge for SickKids 01:13 Meet Alison Simpson and her unconventional career journey 03:23 How Alison became an endurance athlete 05:01 Running 250 kilometres across the Sahara Desert 06:39 The early warning signs of brand and culture misalignment 09:00 Experiencing the customer journey before leading the team 12:45 How accountability builds trust throughout an organization 16:43 Why marketing still fights for strategic influence 18:05 Speaking the language of revenue, profit, and business growth 24:04 How businesses can measure marketing ROI 26:14 Rewirement and saying yes before you feel ready 31:08 Travel, meaningful experiences, and a priceless family memory 35:11 Is this hard, or is it harmful? 41:22 Ambition, integrity, and building a career without a ladderConnect with AlisonLinkedIn: https://www.linkedin.com/in/alisonksimpson/  Connect with UsLinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What if the greatest thing a leader could give their team was not an answer, but the space to discover one?In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Christine Vigna, Chief People Officer at Dejero, to explore leadership coaching, employee empowerment, workplace culture, governance, and the connection between employee experience and business performance.Christine explains why Dejero developed its leaders to become better coaches instead of simply better managers. By moving decisions away from leadership bottlenecks and empowering employees to solve problems, the company has strengthened engagement, accelerated development, improved customer experiences, and achieved employee retention two to three times longer than the average stay in the technology sector.She also shares why culture cannot be separated from business performance, how ego quietly erodes psychological safety, and why confident leaders create space for other people’s ideas rather than needing to be the smartest person in the room.This conversation offers a human-centered approach to leadership that does not sacrifice accountability or results. It shows how thoughtful coaching, consistent governance, and trust can help people perform at their best while building a stronger, more scalable organization.You’ll hear about:How employee experience influences customer experience and revenue Why governance supports scalable, consistent decision-making The question leaders should ask before sacrificing long-term capability How coaching became a driver of business performance at Dejero Why managers become bottlenecks when every decision flows upward How leadership coaching improves autonomy, engagement, and retention Why performance challenges should never surprise an employee How Dejero achieved retention two to three times the technology-sector averageThe difference between confidence and ego in leadership How executive behaviour shapes psychological safety and workplace culture Why coaches help people uncover answers instead of supplying them How to move forward without perfect information or perfect conditionsWe talk about:00:00 Intro 01:13 Meet Christine Vigna, Chief People Officer at Dejero 02:26 Connecting people, customer support, and corporate governance 05:00 Are you solving today’s problem at tomorrow’s expense? 06:16 A customer experience lesson from Mid-Day Squares 09:34 Why governance becomes easier when people see progress 12:41 Aligning business strategy with human-centered practices 14:02 Developing better coaches instead of better managers 15:38 How coaching improved engagement, performance, and retention 21:21 Why every leader can benefit from coaching 24:46 How managers unintentionally become decision-making bottlenecks 28:57 Why ego quietly destroys culture and psychological safety 32:49 Moving forward without perfect conditions or complete informationConnect with ChristinaLinkedIn: https://www.linkedin.com/in/christinemvigna/ Website: https://www.dejero.com/leadership/christine-vigna/  Connect with UsLinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group