00:00:00 Introduction and Context on GTM Team Upskilling

The conversation opens with a discussion about a recent Gartner study indicating that about 70% of Go-To-Market (GTM) teams feel under-skilled for their roles. The guest explains that this spans marketers, sellers, and customer success teams who often feel unprepared for modern demands. A prime example is that many recent graduates have only experienced remote selling and now struggle with in-person interactions. This gap is not limited to newcomers but also affects experienced professionals adjusting between remote and in-person modalities.

00:02:00 The Impact of Digital Transformation on Sales and Marketing Roles

The guest elaborates that the skills gap affects all experience levels due to the rapid digitalization of sales and marketing. New digital-focused roles, such as content creation and podcast hosting by salespeople, have emerged, reflecting a shift in buyer education and engagement strategies. Conversely, experienced sellers face challenges adapting to remote sales enablement and training. Technology alone cannot solve these skill deficits; meaningful training and skills development are essential.

00:04:30 Sales Assembly’s Role in Skills Development and Community Building

Sales Assembly is introduced as a platform offering role-specific skill development across various GTM roles, supplemented by peer-to-peer community sessions. These monthly sessions facilitate knowledge sharing, especially around new technologies like AI and tools such as ChatGPT, which have quickly become mainstream in sales and marketing but require collective learning due to their novelty.

00:06:30 Guest’s Career Journey and Marketing Experience

The guest shares her career trajectory, starting from selling print ads in a parenting magazine without marketing support, giving her full-funnel experience. She transitioned to fintech marketing, agency work, and eventually to managing ABM (Account Based Marketing) programs. This journey highlights the importance of mentorship, executive buy-in, and evolving marketing skills, culminating in her current demand generation role at Sales Assembly.

00:09:40 Account Based Marketing (ABM) Strategy at Sales Assembly

The guest discusses the foundational elements of ABM: solid messaging, targeted account identification, and efficient demand programs. Sales Assembly focuses on a total relevant market (about 3,000 accounts) rather than a broad total addressable market. Initial programs target pipeline generation and thought leadership, with plans to launch industry-specific ABM efforts, especially toward high-growth sectors like AI.

00:12:50 The Concept of “Scrappy ABM”

“Scrappy ABM” is defined as a mindset and approach that enables launching ABM programs with existing resources and technology without heavy upfront investment. Tactics include using podcasts, newsletters, and webinars to build one-to-one relationships with target accounts. The guest shares a personal example of how a low-cost podcast strategy generated significant revenue over 18 months by building trust and relationships instead of immediate selling.

00:18:00 Additional Scrappy ABM Tactics and Overcoming Hesitations

The conversation addresses hesitations around podcasting and content creation, emphasizing that initial imperfection is normal and improvement comes with practice. The guest encourages embracing learning curves. She also shares how podcasts facilitate genuine relationship-building with target buyers by focusing on career growth conversations rather than direct sales pitches.

00:21:30 Building Relationships with Target Accounts

Two approaches are outlined: interviewing hiring leaders to place talent (thus creating advocates) and inviting target accounts to share success stories on skill development. Both approaches avoid sales pitches and instead build trust and long-term relationships, often leading to referrals within tight-knit B2B tech communities.

00:25:30 Leveraging LinkedIn for ABM and Relationship Building

The guest explains a LinkedIn-focused ABM tactic involving sending many connection requests without messages to increase acceptance rates, engaging consistently with target accounts’ content over months, and eventually initiating personalized direct messages. This long-term engagement builds authentic relationships and increases inbound opportunities from target accounts.

00:29:30 Short-Term ABM Plays and Using CRM Data

For quicker results, the guest recommends prospecting within existing CRM contacts to target brand-aware accounts for faster pipeline generation. She also discusses following up with prospects who engage with content by sending tailored messages and relevant gated/un-gated content to nurture interest over time.

00:33:30 Transition from Scrappy to Scalable ABM

The guest outlines benchmarks for scaling ABM programs, such as generating consistent pipeline ($500K+ per quarter) and maintaining conversion rates. At this stage, investing in technology or additional headcount becomes justified for better channel scaling and reporting, moving beyond scrappy tactics.

00:37:00 Organizational Alignment and Empathy for Sales

A critical challenge is internal alignment, especially empathy for sales teams. Marketers must understand sales dynamics and fears, particularly when ABM programs impact sales reps’ pipelines and compensation. Starting ABM pilots with either top or low performers who are open to collaboration helps build internal case studies and executive buy-in.

00:41:30 Engaging Sales Reps and Scaling ABM Adoption

To gain sales rep buy-in, begin with those open to experimentation and build success stories demonstrating improved performance. These case studies encourage broader adoption and advocacy from sales leadership, making ABM a shared organizational priority rather than a side project.

00:44:45 Measuring ABM Program Success

The guest shares metrics to evaluate ABM effectiveness across stages: early-stage content engagement, mid-stage marketing-sourced pipeline, and late-stage marketing-sourced revenue. She cites Sales Assembly’s recent increase in marketing-sourced pipeline as evidence of program success, emphasizing that ABM extends beyond lead generation to supporting deal closure.

00:47:50 Summary and Closing Remarks

The conversation wraps with appreciation for the practical, tactical advice shared. The guest reiterates the importance of long-term relationship building over quick wins and encourages marketers to focus on authentic engagement strategies tailored to their target accounts. This chapter-wise summary captures the progression from understanding GTM skill gaps, through practical ABM strategies, to organizational alignment and measurement — offering a comprehensive guide to modern marketing and sales enablement challenges and solutions.

Profile Mason Cosby CEO & Founder at Scrappy ABM LinkedIn

Mason Cosby is the CEO of Scrappy ABM, helping B2B teams run high-impact account-based programs with lean resources. He focuses on aligning sales, marketing, and customer success to drive measurable pipeline and expansion. Mason is known for his “scrappy” execution style—repurposing content and channels instead of over-relying on complex tech stacks. He shares practical frameworks that help companies move quickly from ABM strategy to repeatable, real-world results.

Show Notes -

This episode is about running effective marketing without heavy tech stacks, big budgets, or large teams. Mason shares how to build real relationships, generate pipeline, and support sales even when resources are tight.
We talk about long-term trust, content that creates connections, and how to make ABM practical instead of overwhelming.

What you’ll learn:
-Why most GTM teams feel under-skilled right now — and what to do about it
-How to start ABM using the tools you already have
-How podcasts, LinkedIn, and ongoing conversations drive real pipeline
-When to scale from scrappy → structured, and what signals to look for

Links & Resources -