Navigating the high-pressure world of sales, marketing, and operations can feel daunting for companies of all sizes. But with the right mix of focus, strategy, and innovation, it’s possible to turn complexity into opportunity. Jared Barol, a seasoned go-to-market (GTM) expert, offers precisely that—insightful strategies for entrepreneurs and executives alike.

From his entrepreneurial beginnings to leading multi-billion-dollar GTM functions at Salesforce Industries, Jared shared tactical advice during his recent conversation with Stephen Lowisz on GTM Secrets. This extended guide breaks down the conversation’s key takeaways, adding even more actionable tips and an emphasis on how to execute these concepts in real-world scenarios.  

Path to Expertise  

Every career trajectory tells a story, but few are as varied and rich as Jared’s. He began as an entrepreneur in industries unrelated to tech—think wine imports and last-mile cheese delivery. These experiences taught him the fundamentals of building a business. Over time, he pivoted, consulting for B2B SaaS companies on market entry strategies across Europe, the Americas, and beyond.  

Jared eventually made the leap into Salesforce, where he led GTM strategies for industry-specific clouds like Financial Services Cloud and Health Cloud—an operating unit responsible for generating $4 billion in annual revenue. His next chapter at Reputation made him a key player in an emerging yet fragmented industry of reputation and social management. With these diverse experiences, Jared is uniquely equipped to identify levers for success across companies of any size.

The Journey to GTM Innovation  

GTM strategies differ significantly between large enterprises and startups—a critical point Jared highlighted. Here’s how those differences play out and what each type of organization can learn.  

For Large Enterprises: Innovation Requires Heavy Lifting  

When a company reaches the size of Salesforce, change—and by extension, innovation—becomes far more difficult. With tens of thousands of employees, even small adjustments come with heavy change management costs. Jared pointed out the importance of separating product innovation from GTM innovation.  

Tactics for Driving GTM Innovation at Scale:  

1. Scenario-based strategy planning: Take a forward-looking approach. Engage futures labs or scenario teams to predict industry trends and reposition your GTM teams early.  
2. Customer-centered workflows: Map each stage of your sales cycle meticulously. For a company as large as Salesforce, success depends on breaking the steps down so every customer-facing team knows exactly where and how they add value.  
3. Leverage ecosystems: For enterprises, GTM success often lies in synergy. Create broader technology ecosystems that keep customers engaged across multiple use cases rather than relying on deep specialization in one product.  

While GTM innovation may be slower and more rigid in enterprises, Jared emphasized that functional alignment gives companies like Salesforce an enduring edge over the competition.

For Startups: Lean into Focus and Execution  

Startups, on the other hand, must avoid the temptation to spread themselves too thin. “You only have so many at-bats,” Jared explained. For smaller businesses, the name of the game remains single-minded execution—mastering your first ICP before making any moves to expand horizontally.  

Steps to Nail Startup GTM:  

1. Choose an ICP strategically: Start small. Even if your product could benefit everyone, focus a surgical sales motion on a high-probability customer base.  
2. Validate repeatability: Before thinking about bigger conquest campaigns or territory expansion, make sure there’s a clear, repeatable GTM motion in your chosen ICP. This includes proven messaging, clear sales playbooks, and accurate forecasting.  
3. Monitor trial signals: Pay attention to inbound inquiries or unintentional wins from unexpected segments. Treat these as opportunities to test target market expansion in smaller experiments before pivoting fully.  

Tactical Expansion Strategies:  

For startups ready to expand after nailing their initial ICP, Jared suggests an iterative approach rather than jumping headfirst into hyper-verticalization.  

• Dedicate single sales reps or pilot teams to new customer profiles or industries without entirely realigning your team or GTM infrastructure.  
• Use localized campaigns to test new messaging and position one-off offerings without risking churn within your existing customer base.

Key Insight: Master one motion before moving to the next. Hypergrowth does not mean attempting to cater to every segment at once.

Building an Effective Sales Enablement Framework  

Jared touched on a critical but often overlooked component of GTM strategy—sales enablement. Small and large companies alike mismanage this function, leaving sellers under-equipped to scale, cross-sell, or even onboard efficiently.  

Why Sales Enablement Matters  

Sales enablement ensures your GTM strategy is not only well-designed but also executable. It bridges the gap between leadership’s vision and frontline execution. Jared described Salesforce’s system as having every buyer stage mapped, with content and functionality aligned to specific sales motions, ensuring no resource is out of place.  

How Startups Can Prioritize Enablement  

Startups often wait too long to invest in enablement. According to Jared, the magic number is 15–20 reps. At that point, tactical training, content creation, and onboarding start to consume more time than managers or product teams can handle.  

Steps to Build Enablement from Scratch:  

1. Define measurable KPIs: Tie every enablement activity to a performance goal. Examples include time-to-ramp for new hires or cross-sell growth after skill-based training.  
2. Start small: Your first enablement hire doesn’t need flashy tools. A single full-time role can address process improvement, build training collateral, and start coaching across geographies.  
3. Layer in advanced tools slowly: For larger teams, automate what you can. Jared recommends tools like Gong (for call coaching) or even CRM-integrated enablement platforms once your team passes 30–50 salespeople.  
4. Pilot first, scale later: Before fully rolling out training or playbooks, test small groups or sub-teams to troubleshoot gaps and refine delivery before larger adoption.

Metrics to Leverage:  

For startups struggling to connect enablement spend with revenue, reference CRM adoption, quota attainment, and product knowledge surveys to showcase progression.

For enterprises like Salesforce, where ecosystems are more sophisticated, Jared emphasized competitive benchmarking. Enablement not only helps internal teams sell more effectively but also ensures winnable customers do not slip through the cracks in saturated territories.

Implementing Account-Based Marketing (ABM)  

ABM is one of the most potent weapons in a SaaS marketer’s arsenal. Jared argued that generic outbound strategies waste not only budget but also the market’s attention spans. Instead, he doubled down on ABM as the only way to maximize ROI in competitive markets.

Tactical Steps to Launch ABM Successfully:  

1. Account prioritization: Start with a tightly-defined ICP, then narrow this down further into a target account list that has the highest propensity to buy. Jared compared choosing ABM targets to spending $20 per prospect versus $1 in traditional outbound—less spray, more win.  
2. Cross-team alignment: Engage your product, marketing, and sales teams early to define messaging relevant to key accounts.  
3. Personalization trumps volume: Customize outreach specifically to decision-makers’ challenges. This can be achieved with tailored assets (whitepapers, case studies) or direct consultative sales offers like strategy sessions.  
4. Measure deal velocity: Monitor how quickly accounts are progressing through the pipeline to compare ABM outcomes versus other strategies.  
5. Iterate often: Not every industry or ICP will respond uniformly to ABM efforts. Track granular data, such as engagement by role or type of campaign personalization, and pivot often.

For startups, ABM is an effective way to punch above their weight when competing against larger platforms. For enterprises, it’s the key to making sure your massive investment in sales doesn’t spread too thin.

Companies must walk a fine line between sustaining what works and exploring what could work better.  

For Startups:  Lean directly into agility and speed. When trying new motions, fail fast, collect data from each experiment, and avoid fixating on expansion until the numbers justify it.

For Enterprises:  Your sandbox should be just as bold, but cost reductions and implementation logistics often become higher priorities as you scale. Rather than seeking disruption for disruption's sake, Jared advises pursuing cross-functional innovation that amplifies stable business units over time.

Final Words:  Jared’s GTM strategies blend focus, innovation, and execution into a winning formula for both startups and enterprises. Whether you’re building a team from scratch or refining a massive sales engine, the principles are the same. Nail one motion, enable your team robustly, and remain disciplined even while ambitious. Reaching the next level will always depend on how well you execute the level you’re at today.  

Your GTM playbook is in your hands—are you ready to level up?  

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