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

About Guest

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.

A glimpse of what you will learn

• [1:20] Usman Sheikh shares his background as a serial entrepreneur and the vision for Agentive
• [2:49] The difference between AI agents and Agentive’s outcome-driven model
• [5:01] Why companies misuse AI by focusing on task automation instead of process transformation
• [6:25] Identifying broken elements in B2B sales workflows and the importance of rolling pipelines
• [8:38] Using Agentive’s AI engine to create ideal customer profiles and uncover new opportunities
• [20:16] Leveraging AI research to deliver daily sales recommendations and outreach campaigns
• [28:40] Key KPIs for measuring success with Agentive in sales organizations

Resources Mentioned in this episode

• T.A. Monroe Digital Agency
• Alex Gluz on LinkedIn
• Usman Sheikh on LinkedIn
• Agentive
• Salesforce
• HubSpot
• ChatGPT

Quotable Moments

• "AI is such a big transformational force, and it has the ability to perform multiple tasks at the same time."
• "Only 70% of B2B sales reps did not make their quota last year, so obviously there's something broken."
• "Something that takes 3-4 weeks to do can be reduced into less than a minute."
• "Better intelligence, better capabilities, more time, and more opportunities all add up to a higher conversion ratio.
• "The sooner we can start focusing on results and outcome, the better the business is going to move."

Action Steps

1. Reimagine your sales process end-to-end: Designing AI strategies around outcomes instead of tasks ensures technology drives measurable business results.
2. Build and maintain a rolling pipeline: A consistent flow of qualified opportunities prevents revenue gaps and reduces the risk of sales cliffs.
3. Automate ideal customer profiling: Leveraging AI to identify high-value prospects saves time and improves the precision of targeting efforts.
4. Use AI recommendations to guide daily actions: Structured, data-driven prompts help sales teams focus on high-impact activities that boost conversion rates.
5. Track KPIs like revenue and pipeline health: Monitoring these metrics validates AI effectiveness and aligns sales activities with organizational growth goals.

Sponsor for this episode

This episode is brought to you by T.A.Monroe Digital.At T.A.Monroe, we build world class revenue engines for B2B SaaS companies. What that means is we do everything behind the scenes to generate you tons of qualified leads, opportunities and customers.

1. We build highly effective marketing systems and scale their profitably through our demand generation strategies.
2. We think scientifically on how to scale your demand and revenue.
3. We bring decades of experience.

Email us at alex@tamonroe.com or visit www.tamonroe.com today to schedule a strategy session or learn more about our mission.