Fixing Broken B2B Sales Workflows With AI-Powered Strategies With Usman Sheikh

Christine Royston is the Chief Marketing Officer at Wrike, an intelligent work management platform that helps teams build, connect, automate, and scale workflows. She joined in June 2024 after more than 20 years in B2B enterprise marketing. Before Wrike, Christine was VP and Global Head of Marketing at Udemy, where she helped grow annual recurring revenue from $100M to over $450M and led initiatives including an IPO and rebrand. She also held leadership roles at Bitly, Dropbox, Imperva, and Salesforce. In this episode… In today’s marketing landscape, every dollar spent is under a microscope, and leaders are under pressure to prove impact faster than ever. How can CMOs align their budgets, metrics, and customer strategies to show real business value while navigating constant change? According to Christine Royston, a seasoned B2B marketing leader with global experience, the key is balance. She emphasizes that marketing must be both data-driven and customer-focused, ensuring pipeline and bookings remain at the center of conversations with executives. She highlights how aligning budgets with measurable outcomes builds trust across the business and creates room for innovation. By focusing on efficiency, clear communication, and proactive performance tracking, marketing leaders can demonstrate value early and often. In this episode of the Revenue Engine Podcast, host Alex Gluz sits down with Christine Royston, Chief Marketing Officer at Wrike, to discuss how CMOs can align budgets, metrics, and customer value. She explains why data transparency builds stronger executive relationships, how to balance brand and demand generation, and the role of customer-centric thinking in growth. Christine also shares insights on adapting to AI-driven changes in marketing.

Usman Sheikh is the Founder and CEO of Agentive, a next-generation AI platform that helps B2B companies generate pipeline, identify quality leads, and accelerate sales outcomes. A serial entrepreneur based in Silicon Valley, he specializes in building businesses at the intersection of AI and enterprise sales and marketing. Agentive envisions AI agents seamlessly collaborating to support revenue teams with a measurable, results-focused impact. This is Usman’s fourth startup, reflecting his deep experience in creating and scaling innovative technology ventures. In this episode… Too many sales teams struggle with missed quotas, inconsistent pipelines, and wasted hours on administrative tasks. Even with AI tools at their disposal, companies often see little improvement in outcomes. Is the problem with the technology or with how it’s being applied? According to Usman Sheikh, a serial entrepreneur who has built multiple ventures at the intersection of AI and B2B sales, the core issue is that most companies use AI to replicate human tasks instead of reimagining entire sales processes. He highlights that focusing solely on task automation leads to fragmented workflows and lost opportunities, while an outcome-driven approach can transform the entire sales cycle. By building systems that integrate ideal customer profiling, opportunity identification, and daily recommendations, sales teams can spend more time engaging prospects and less time bogged down in admin work. This shift not only increases efficiency but also improves conversion rates and revenue predictability. In this episode of the Revenue Engine Podcast, host Alex Gluz sits down with Usman Sheikh, Founder and CEO of Agentive, to talk about fixing broken B2B sales workflows with AI-powered strategies. They explore why traditional sales processes fail, how to build and maintain a rolling pipeline, and ways AI can enhance sales performance without replacing human judgment. Usman also shares key KPIs for measuring the impact of AI in sales organizations.

Kristin Oelke is the Managing Director for Growth Services at Brightrose Ventures, an enterprise software advisory and investment firm that provides strategic guidance, fractional executive teams, and execution support to mid‑market business software companies. In 2024, her firm Green Street Advisors merged with Brightrose to expand its reach and deliver efficient, trust‑driven marketing capabilities to investors and management teams. At Brightrose, Kristin leads go‑to‑market advisory services and is the author of Trust: Unlocking B2B Growth in Today’s AI World. In this episode… Trust is the invisible force that drives B2B growth. But in an AI-driven world flooded with content, automation, and noise, earning that trust is more difficult than ever. How can companies prove their value and credibility when buyers are skeptical and overwhelmed by options? According to Kristin Oelke, a B2B growth strategist and marketing expert, trust is built through validation — not volume. She highlights that companies struggling to move prospects through the funnel often lack the third-party proof, consistent messaging, and real-time feedback mechanisms that signal credibility. The result is a stalled pipeline, even when product-market fit exists. Kristin emphasizes that building a “public trust profile” is essential, especially in complex B2B sales, and that trust can only be earned when happy customers, aligned teams, and transparent data come together to support the brand promise. In this episode of the Revenue Engine Podcast, host Alex Gluz is joined by Kristin Oelke, Managing Director for Growth Services at Brightrose Ventures, to talk about why trust is more important than ever for growth in today’s AI-driven world. They discuss how companies can actively manage their public trust profile, align cross-functional teams around shared goals, and use AI without losing the human element. Kristin also shares insights on helping companies navigate strategic pivots.

Mike Braund is the Senior  Director of Marketing Operations and Digital Marketing at Iterable, an AI-powered, multi-channel communications platform. He leads cross-channel orchestration efforts, overseeing Martech, account management, email, web, and analytics to drive pipeline growth and operational efficiency.  In this episode… Standing out in B2B SaaS marketing requires mastering more than just performance metrics and automation tools. With budgets tightening and the buyer’s journey growing longer, how do leading marketers balance long-term brand building and short-term revenue generation? According to Mike Braund, a seasoned marketing leader with a deep background in operations and analytics, achieving that balance starts by connecting data with gut instincts. He highlights the importance of testing hypotheses quickly through iterative campaigns, using data to validate direction without stalling creative momentum. This blend ensures marketing efforts perform and resonate. Creative constraints can unlock innovation, especially when teams are empowered to move fast with limited resources. In this episode of the Revenue Engine Podcast, host Alex Gluz sits down with Mike Braund, Senior Director of Marketing Operations and Digital Marketing at Iterable, to discuss how to align brand and performance marketing in B2B SaaS. They dive into the role of data-informed creativity, how team structure can enable efficiency, and the importance of full-funnel thinking. Mike also shares lessons from leading paid media and operations under one unified strategy.

Ani Obermeier is a Board Advisor at WorkBuzz, a company that provides real-time employee feedback and engagement solutions for organizations with deskless, hybrid, and remote workforces. She brings over 15 years of experience in technology marketing, having held leadership roles at companies like Workday and Peakon. Currently, Ani serves as Chief Marketing Officer at Quinyx, where she leads strategic marketing initiatives to drive business growth. In this episode… Cutting through the noise is one of the greatest challenges for modern B2B brands. In industries crowded with similar offerings and endless noise, what actually makes one company stand out over another? Is it product features, pricing, or something more human? According to Ani Obermeier, a seasoned marketing strategist and board-level advisor, the true differentiator is trust built through authentic, emotionally resonant communication. She highlights that most B2B companies focus too much on themselves while ignoring the human decision-makers on the other end. Instead of obsessing over competitors, Ani urges brands to listen deeply to their buyers, speak their language, and focus on building long-term relationships. In doing so, businesses not only differentiate but also stay relevant in markets where feature parity is the norm. In this episode of the Revenue Engine Podcast, host Alex Gluz sits down with Ani Obermeier, Board Advisor at WorkBuzz, to talk about building trust and standing out in saturated markets. They explore how to unify sales and marketing teams under a single go-to-market strategy, why authenticity beats automation, and what makes messaging truly connect. Ani also shares how cultural nuance shapes global marketing success.

Sylvia LePoidevin is the CMO at Kandji, a B2B SaaS company that provides Apple device management and security automation for IT and security teams. She joined Kandji as its fourth employee and rose to CMO by her late twenties, leading marketing during its rapid growth to an $850 million valuation. Before Kandji, Sylvia held key product marketing roles at DataFox and Oracle AI and was the first marketing hire at FloQast, now a billion-dollar company. In this episode… Standing out in B2B marketing has never been more difficult or more essential. With noise at an all-time high and AI reshaping content at scale, how can marketing leaders create lasting brand impact and foster genuine community around their companies? According to Sylvia LePoidevin, a seasoned marketing leader who has scaled multiple brands from the ground up, the key lies in focusing on people-first branding and building content engines powered by strategic AI use. She highlights the importance of empowering internal influencers and subject matter experts to lead brand storytelling, rather than relying solely on corporate messaging. The result is a more authentic and differentiated brand presence that cuts through digital clutter. Sylvia also emphasizes the value of niche-focused communities and original content anchors as foundations for an efficient, AI-enhanced content flywheel. In this episode of the Revenue Engine Podcast, host Alex Gluz sits down with Sylvia LePoidevin, CMO at Kandji, to talk about reinventing modern B2B marketing through branding, community, and AI. They discuss why people — not logos — build the strongest brands, how anchor content drives scalable distribution, and why marketers must continuously reinvent themselves to lead effectively. Sylvia also shares insights on navigating long buyer journeys and rising acquisition costs.

Nick Naso is the Chief Revenue Officer at Recurly, a leading subscription management and billing platform that helps businesses automate and optimize recurring revenue operations. With over 15 years of experience in the software and technology industry, he has built high-performing teams and led strategic initiatives to drive significant growth. Before joining Recurly, Nick served as Chief Revenue Officer at Cayuse, where he led the global sales organization and helped the company achieve record revenue growth through new customer sales and geographic expansion. In this episode… Understanding your ideal customer profile can make or break your B2B SaaS growth strategy. Without clarity around who you're selling to, it's easy to waste time, miss revenue targets, and stall your momentum. So how often should companies revisit and refine their ICP to keep pace with a fast-changing market? According to Nick Naso, a seasoned revenue leader with deep experience in scaling SaaS companies, companies should formally reevaluate their ICP at least once or twice a year. He highlights the importance of ongoing data analysis to inform micro-adjustments before larger shifts are needed. This kind of consistent review ensures sales teams focus on high-fit prospects and avoid spending resources on poor matches. The result is tighter alignment, faster sales cycles, and stronger pipeline efficiency. He also emphasizes that fit is everything: the right customer at the right time drives not only sales, but long-term success. In this episode of the Revenue Engine Podcast, host Alex Gluz is joined by Nick Naso, Chief Revenue Officer at Recurly, to discuss why a sharp ICP is central to B2B SaaS growth. They explore how to identify ICP signals from pipeline data, when to make structural changes in your team to match your market, and why sales success starts with strategic focus. Nick also shares insights on leading cross-functional teams and building a culture of revenue ownership.

Patrick Ferdig is the Founder and Principal Consultant at The Power of Partnering, a firm dedicated to helping B2B technology and service providers build and scale effective partner-led growth strategies. With over two decades of experience in the technology industry, Patrick specializes in developing partner programs — including reseller channels, integration marketplaces, and referral networks — that drive revenue and innovation. His approach is grounded in five core principles: trust, alignment, collaboration, accountability, and facilitation, which he applies to help organizations unlock their full potential through strategic partnerships. In this episode… As traditional sales and marketing tactics reach their limits, businesses are looking for smarter, more sustainable ways to grow. What really makes a partnership thrive in today’s crowded and complex market? According to Patrick Ferdig, a veteran partnership strategist and consultant, it all starts with trust. He highlights that internal alignment across teams is just as crucial as external collaboration. Without a clear structure and shared understanding of goals, even the most promising partnerships can falter. Patrick explains that the most successful companies treat partnerships as a core growth strategy, not a side initiative. He also emphasizes that revenue impact doesn’t come from signing more partners but from engaging deeply with fewer, well-matched ones. In this episode of the Revenue Engine Podcast, host Alex Gluz speaks with Patrick Ferdig, Founder and Principal Consultant at The Power of Partnering, to discuss the five pillars of partnership success. They explore why trust drives results, how alignment shapes execution, and what businesses must prioritize to turn partners into revenue engines. Patrick also gives advice on scaling outreach using AI tools.

Mark Stiltner is the Senior Director of Content and Web Marketing at Rapyd, a global fintech company that simplifies and advances commerce by providing integrated payment and fintech solutions across over 100 countries. With a background in advertising and journalism from the University of Colorado Boulder, he has led creative and brand strategy initiatives across multiple industries. Prior to joining Rapyd, Mark held leadership roles at agencies like Karsh Hagan and Market Creation Group, where he developed award-winning campaigns and drove brand growth. At Rapyd, he oversees content strategy and digital marketing efforts, helping businesses navigate the complexities of global payments and cross-border commerce. In this episode… In today’s fast-changing digital world, marketers face a growing challenge: how do you stay ahead when AI is rewriting the rules of SEO, content, and customer engagement? As traditional tactics lose traction, brands must rethink their strategies to remain visible and relevant. What does it really take to build a content engine powered by AI that drives results instead of noise? According to Mark Stiltner, a veteran content strategist, building an AI-driven content engine starts with experimentation and adaptability. He highlights the importance of using AI not as a replacement for creativity, but as an accelerator for research, ideation, and production. The key, he explains, is integrating AI tools thoughtfully into workflows while keeping human insight at the center to maintain authenticity and relevance. This balanced approach allows teams to scale content efficiently without sacrificing quality, enabling marketers to respond faster to shifting algorithms and buyer behaviors. Mark also emphasizes the growing need to optimize not just for search engines, but for AI models driving new traffic sources. In this episode of the Revenue Engine Podcast, host Alex Gluz speaks with Mark Stiltner, Senior Director of Content and Web Marketing at Rapyd, to talk about building an AI-powered content strategy. They discuss weaving AI into SEO workflows, shifting from traditional search optimization to AI model visibility, and balancing automation with creativity. Mark also shares practical ways to future-proof marketing teams in an AI-driven landscape.

Bethany Prettyman is the Senior Director of Marketing Operations at Huntress, a cybersecurity company specializing in managed detection and response solutions for small and mid-sized businesses. With a robust background in strategic operations, she leads initiatives that enhance marketing efficiency and drive growth. Bethany's leadership ensures that Huntress's marketing strategies effectively communicate the company's mission to protect underserved organizations from cyber threats. In this episode… The traditional B2B marketing funnel might be doing more harm than good. In an era of complex buyer journeys and intent-driven decisions, is it still realistic, or even useful, to imagine prospects moving through neat, linear stages? What if the funnel model we’ve relied on for decades is actually leading marketing ops teams astray? According to Bethany Prettyman, a seasoned expert in marketing operations and data-driven strategy, the funnel is no longer linear, it’s a loop. She highlights how today’s B2B buyers bounce between channels, revisit research, and often re-enter the journey post-purchase, making linear tracking obsolete. The result? Misaligned attribution models and missed opportunities to optimize real engagement. Bethany explains that the obsession with MQLs is outdated and that teams should instead prioritize intent and velocity, focusing on signals that indicate purchase readiness rather than arbitrary lead scores. This mindset shift not only improves conversion but also strengthens alignment with sales. In this episode of the Revenue Engine Podcast, host Alex Gluz speaks with Bethany Prettyman, Senior Director of Marketing Operations at Huntress, to discuss why the traditional B2B funnel is broken. They explore why loop-based models better reflect today’s buyer behavior, how attribution should evolve, and the dangers of tech bloat in marketing stacks. Bethany also shares her agile approach to reporting and how to bridge gaps between sales, marketing, and finance.