Getting to your first wins feels like momentum. Scaling past $50M exposes everything that is not built to last.

On this episode of WinsDay, Jessie Lizak sits down with Kris Rudeegraap, Co-CEO and Co-Founder of Sendoso, and Mariam Slimane, CMO and Growth Marketing Advisor at CX Fractional Advisors, to break down what actually drives pipeline and revenue as companies grow.

Kris shares his journey from sales rep to building Sendoso into a category leader, offering a firsthand look at how sales strategy evolves as companies scale.

The conversation explores how AI-powered direct mail and gifting help sales teams cut through noise, create meaningful engagement, and move deals forward in competitive markets.

Mariam brings deep experience in scaling B2B SaaS companies from $50M to $100M+ ARR. She focuses on building AI-driven demand generation systems, aligning product-led growth with enterprise GTM strategy, and creating marketing engines that produce a predictable pipeline. She also addresses a common issue in growth teams, over-reliance on CRM data, which often leads to missed demand signals and weaker pipeline performance.

Together, the discussion explores:

1. AI-Powered Direct Mail for Sales Teams

2. Over-Reliance on CRM Data Hurts Pipeline Growth

3. From Sales Rep to $100M CEO

4. Why Growth Stalls After $50M

This episode focuses on what changes between early traction and scalable growth, from pipeline strategy and demand generation to marketing systems and execution discipline.

For founders, revenue leaders, and B2B operators, the conversation offers a clear look at what it takes to move beyond founder-led momentum and build systems that support long-term growth.

B2B growth has shifted as AI accelerates execution while buyers become more informed, selective, and self-directed throughout the decision-making process.

Traditional playbooks built around volume, funnels, and isolated campaigns no longer hold the same weight, creating a need for more precise, structured, and consistent approaches to marketing and go-to-market strategy.

On this episode of WinsDay, Jessie Lizak sits down with Alexander Shartsis, Co-founder and CEO of Skyp.ai, and George Couris, President and CEO of The Pepper Group, to unpack how modern B2B growth actually works right now.

Alex brings a builder and operator perspective. From bootstrapping to working with top VCs, raising capital, exiting, and even shutting companies down, he has seen the full lifecycle.

Through Skyp.ai, he focuses on helping founders and sales teams run targeted microcampaigns that drive engagement. The conversation dives into how go-to-market strategy with AI is changing execution, how outreach needs to adapt to today’s buyer, and why precision matters more than volume.

George brings nearly three decades of experience leading a full-service B2B marketing agency. At Pepper Group, he has worked with companies across industries on branding, lead generation, market expansion, and marketing strategy.

He shares how content strategy continues to evolve as buyers become more self-directed, why consistency and clarity outperform scattered campaigns, and how disciplined marketing systems influence investor confidence during due diligence.

Together, the discussion explores:

1. Go-to-Market Strategy with AI

2. Evolving B2B Content Strategy for Modern Buyers

3. Effective Outreach for Today’s Market

4. Disciplined Marketing Systems Signal Investor Readiness

This episode connects AI-driven execution, content strategy, outreach performance, and marketing maturity into one clear theme: growth comes from structure, relevance, and consistency.

For founders, CEOs, CMOs, and B2B marketing leaders, this conversation delivers practical insight on building go-to-market systems, improving outreach, aligning content with buyer behavior, and creating marketing engines that support long-term growth and investor readiness.

Attention is easy to buy. Trust is harder to earn, and even harder to keep.

On this episode of WinsDay, Jessie Lizak sits down with Gal Borenstein, Founder and CEO of The Borenstein Group, and Seva Ustinov, Founder and CEO of Elly Analytics and Plurio AI Agent, to unpack what brand trust looks like in a market shaped by automation, scale, and constant noise.

Gal brings over 30 years of experience advising companies in technology, defense, cybersecurity, and professional services on branding, reputation, and market positioning.

He shares how fake reviews, manipulated social proof, and digital saturation are reshaping how buyers evaluate credibility. The conversation dives into how brands build trust through transparency, consistency, and strong positioning, and how those signals hold up under scrutiny.

Seva brings a performance marketing and execution lens. After shifting his teams to AI-first operations, he focuses on speed, context, and decision-making across complex funnels. He explains how automation, AI agents, and marketing systems impact how brands engage audiences at scale, and where teams risk losing authenticity if execution outpaces strategy.

Together, the discussion explores:

1. Maintaining Brand Trust in a World of Fake Reviews

2. AI-Driven Marketing Automation

3. Maintaining Brand Resilience in the Age of AI

4. AI Agents for Performance Marketing

This episode looks at how trust, performance, and execution intersect, especially as marketing becomes faster, more automated, and more difficult for buyers to evaluate at face value.

For founders, CMOs, and marketing leaders, the conversation offers a grounded perspective on building credible brands, maintaining consistency across channels, and creating marketing systems that support long-term trust and growth.

Revenue problems rarely start in sales. They start upstream

In positioning. In the pipeline structure. In lifecycle gaps. In marketing teams that generate activity but not accountability.

On this WinsDay episode, with Taja M. Graham, Founder and CEO of OpsIQ, and Javier Lozano Jr., Fractional CMO and GTM leader at Bolder Media Co., to unpack what revenue-driven marketing actually requires inside founder-led B2B companies.

Taja brings the operational reality check. Growth breaks when systems lag behind demand. Hiring without structure creates bottlenecks. Marketing pushes leads into pipelines that operations cannot support.

She shares how operational alignment, execution discipline, and capacity planning directly impact marketing performance and revenue growth.

Javier brings the go-to-market framework. After scaling companies from $1M to $20M+ and building 11x pipeline growth, he explains how predictable demand generation, revenue operations, attribution modeling, and lifecycle marketing create consistent SQL conversion and stronger close rates. No random tactics. No campaign-of-the-month resets.

Together, the conversation centers on:

1. Turning Marketing Into Sales Conversions

2. Marketing Accountability for Revenue Growth

3. Key Metrics for Marketing Performance

4. The $2M Lifecycle Strategy That Converts

Expect a practical discussion on B2B marketing strategy, pipeline acceleration, lifecycle revenue systems, RevOps alignment, demand generation, and measurable marketing ROI.

If you are a founder, CEO, CMO, or revenue leader building predictable growth, this episode focuses on structure, metrics, and execution that move marketing from cost center to revenue engine.

B2B marketing continues to evolve. LinkedIn has become a primary platform for sales strategy and personal branding.

Influencer marketing now drives measurable revenue across both B2B and CPG brands. Founders are rethinking how branding, research, and partnerships fuel long-term growth.

On this episode of WinsDay, Eran Mizrahi, CEO of Source86, and Henry Young, Founder and CEO of Avari Research, have a strategic conversation on modern brand growth, LinkedIn sales strategy, and influencer marketing performance.

Eran brings an operator’s perspective from scaling procurement and supply chain operations for major CPG brands selling in retailers like Costco Wholesale, Target, and Trader Joe's.

With experience managing over $100M in procurement and navigating supply chain disruption during rapid growth, he understands how brand positioning, relationship-building, and trust impact long-term revenue.

He shares insights on driving sales through LinkedIn strategy, building credibility in B2B environments, and aligning branding with operational execution.

Henry represents the next generation of marketing leadership. Through Avari Research, he works at the intersection of gaming, social media marketing, Gen Z consumer behavior, and influencer partnerships.

After helping generate more than 1 billion views across campaigns, he focuses on data-driven influencer marketing, audience research, and brand collaboration strategies that resonate with younger consumers. His work centers on measurable campaigns, creator partnerships, and market research that informs smarter influencer selection.

This episode covers:

1. Driving Sales Through LinkedIn Strategy

2. Influencer Marketing

3. The Role of Branding in B2B Startup Growth

4. Market Research for Influencer Brand Partnerships

For founders, CMOs, CPG leaders, B2B startups, and marketing teams, this conversation explores LinkedIn lead generation, personal branding for executives, influencer marketing ROI, consumer research, and scalable brand growth strategies.

If you are building a B2B brand, launching a startup, or expanding through influencer partnerships, this episode delivers practical insights on sales strategy, brand positioning, and performance-driven marketing.

Marketing is changing fast, and most leaders are still figuring out what that actually means for their business.

On this episode of WinsDay, Jessie Lizak sits down with Andrea Dyan Brown, Chief Strategy Officer, and Olivia Yates, Co-Founder of HumanFirst Accelerator, for an honest conversation about where marketing is headed and what to do about it.

Andrea has spent her career at the intersection of strategy and innovation, helping organizations think clearly about AI without either overselling it or ignoring it.

She digs into how AI search is quietly reshaping the way people find brands, and why that matters more than most marketing teams realize.

Olivia brings 15+ years of in-the-trenches marketing experience across startups, tech, hospitality, wellness, and agencies.

She's the kind of marketer who cares just as much about the numbers as the narrative, and in this conversation, she gets practical about customer acquisition costs, multi-channel strategy, and building brand stories that actually connect with people.

Together, they cover:

1. The Shift from Search Engines to AI Search

2. Understanding Customer Acquisition Cost (CAC)

3. AI Marketing Platforms: Promises and Limits

4. Multi-Channel Marketing Strategy

If you're a founder, CMO, or anyone responsible for growth, this one's worth your time.

Sales not converting?

Before you blame the market, your team, or the algorithm…

it might be your messaging.

Or the way you’re testing it.

This episode of WinsDay is all about fixing sales conversions with smarter messaging and structured experimentation.

Joining Jessie Lizak:

Dr Diane Dye, Founder and CEO of People Risk Consulting. Diane works with CEOs and executive teams to build structured experimentation into their strategy so innovation doesn’t turn into chaos. She has advised more than 500 leaders on decision-making, culture, and growth.

Rich M. Smith, MBA, Founder of Rich M. Smith Growth Studio. With 30+ years in high-stakes industries and CMO-level experience, Rich blends behavioral science and executive strategy to help companies understand why their marketing works and where it breaks down.

We’ll cover:

1. Exploring Sales Experimentation Strategies

2. The Science Behind Brand Messaging

3. Marketing Experimentation in Practice

4. Why Sales Pitches Fail to Convert

If you’re leading growth, running GTM, or trying to improve conversion rates, this conversation will challenge how you think about messaging, testing, and what actually moves buyers to act.

Join us live and bring your questions.

Modern brands are not winning because they post more.

They’re winning because their SEO, product strategy, and positioning actually work together.

On this episode, Jessie Lizak is joined by two founders who understand how to turn creativity and strategy into real revenue.

Jacinta Devlin, CEO of Devlin Consulting Group, is a digital marketing strategist and multi-8-figure business consultant who has helped thousands of women entrepreneurs go from idea to income.

She specializes in brand positioning, sales systems that convert, email marketing, and building profitable online businesses without chaos. Her work focuses on launching with clarity, strong messaging, and structured growth from day one.

Latif Hamilton is the Creative CEO of SpiritHoods, a purpose driven fashion brand that has generated over $55 million in revenue.

He has built an iconic ecommerce brand rooted in sustainability, storytelling, and product innovation. Through SpiritHoods and The Growth Operative consultancy, he helps businesses align marketing and product strategy to unlock long term growth and profitability.

Together, they’ll explore:

1. Elevating Your Online Brand for 2026

2. How SEO and Product Strategy Align

3. Building a Professional Brand That Attracts Clients

4. Creative Marketing Without Discounts

If you’re building a brand in ecommerce, coaching, consulting, or B2B and want stronger visibility, better conversions, and sustainable growth, this conversation will give you practical insight you can apply immediately.

Join us live and bring your questions.

The way we lead and market in tech is changing fast.

Founders, executives, and marketers are navigating constant disruption. AI. Web3. Regulation. New buyer behavior. More noise than ever. The question is no longer just how to grow, but how to lead and build with clarity in the middle of it all.

In this upcoming WinsDay, we’re joined by Lauren Friedman and Maria Lobanova for a conversation at the intersection of leadership, innovation, and modern marketing.

Lauren Friedman, Founder and CEO of WHY GO PROJECT — [RE]DEFINING THE HUMAN EXPERIENCE THROUGH THE LENS OF TRAUMA, brings a powerful lens on leadership, nervous system literacy, and human connection. With a background spanning AdTech, emerging technology, and trauma-informed leadership, she challenges the way we think about regulation, anticipation, and how we show up in high-pressure environments.

Maria Lobanova, CMO of Naoris Protocol, leads marketing at the forefront of Web3 and cybersecurity. With deep experience in emerging technology, global campaigns, and community-driven growth, she understands what it takes to build trust, traction, and visibility in fast-moving tech ecosystems.

Together, we’ll explore:

1. Leading from Regulation vs Reactive Anticipation

2. Marketing Strategies in the Web3 Space

3. Anti-Anxiety Networking

4. Modern Marketing in the Technology Sector

If you’re building in tech, exploring Web3, or leading in an environment that demands both innovation and emotional intelligence, this conversation will give you a sharper perspective on what future-focused growth really requires.

Join us live and bring your questions.

Profit and performance don't have to be at odds with ethical leadership. The key is knowing which levers to pull and when to automate with integrity.

In this upcoming episode, we’re bringing together two experts who are redefining how brands scale and how leaders manage in an increasingly automated world.

Matt Slaymaker, Founder of Slaymaker Marketing, is the "no-fluff" strategist for brands tired of hearing excuses about algorithms and learning phases.

Having spoken at Google and led strategy for massive performance agencies, Matt helps companies stop the "leaky bucket" of ad spend. He specializes in cutting through the noise to align offer, creative, and measurement for actual, profitable growth.

Mohamed A. Yousuf, CEO and Founder of Smart Workforce AI, understands that time is a business's most undervalued resource. Drawing from a decade of experience in high-stakes environments like aviation and logistics, Mohamed builds human-centered AI systems designed to modernize decision-making.

His work proves that technology should reduce friction and burnout, returning time and clarity to people.

Together, they’ll bridge the gap between aggressive digital acquisition and sustainable, AI-driven operations.

We’ll cover:

1. Scaling ROI with Google Ads Mastery

2. AI-Enhanced Leadership for Modern Management

3. Mastering Meta: High-Performance Creative Strategies

4. Selling Ethical AI: Strategy and Governance

If you are looking to lower your CAC while simultaneously building a more resilient, AI-ready organization, this conversation will provide the roadmap you need.

Join us live this WinsDay at 8:00 PM and bring your questions.