Scaling a Salesforce team isn’t just about hiring fast—it’s about building a structure that sustains growth and drives measurable outcomes. Whether you’re a VP of Technology, Salesforce consulting firm leader, CIO, or a Salesforce architect, understanding how to scale efficiently can make or break your success.

In a recent episode of the Salesforce Hiring Edge podcast, Josh LeQuire and I sat down with David Kestenberg—a former CIO, Salesforce transformation leader, and five-time Dreamforce speaker. David has scaled Salesforce teams across more than 20 organizations, leading through chaos and driving growth at speed.

This post distills his top strategies for hiring, team building, and leadership development, with practical advice you can implement now.

The Top 2 Pitfalls of Scaling Salesforce Teams

David highlighted two critical risks that leaders face when building Salesforce teams fast:

1. Internal Challenge: Imposter Syndrome Even the most seasoned leaders experience self-doubt: Am I ready for this level of responsibility? David’s advice: continually refine your leadership craft and recognize that personal growth is a constant process.
2. External Challenge: Budget What are your limitations? Is the money there? And if there’s a lot—are you scaling just to scale, or are you scaling responsibly?

“Scaling is not necessarily going from 10 people to 100 people… sometimes it’s going from 10 to 50, but changing roles, ranking, communication, internal processes,” David noted.

Hire for Trajectory, Not Just Today

One standout insight from the episode is David’s emphasis on hiring for future growth. He recommends uncovering each candidate’s North Star—their long-term career aspirations—and integrating that vision into your team planning.

Example Salesforce Career Paths:

• Business Analyst ➔ Senior BA ➔ Product Owner
• Developer ➔ Lead Developer ➔ Architect
• Project Manager ➔ Program Manager ➔ Director of Delivery

By investing in candidates with a clear growth trajectory, you build internal pipelines that reduce turnover and future hiring needs. As David put it (paraphrased): by their 30s, it should already be clear whether someone is on a tech track, leadership track, customer-facing track, etc.

The “Vibe Check” and Cultural Alignment

David uses the term “vibe check” to describe the culture fit assessment that’s crucial for long-term success. Critically, this step only happens after technical competence has been confirmed.

His two-step process:

• Technical Vetting: Conducted by hiring managers and team leads
• Vibe Check: Led by senior leadership to assess growth mindset, cultural fit, and team dynamics

“It’s my role to ensure a new hire will fit both the current team and the future we’re building.”

This process ensures you’re hiring not just skilled Salesforce professionals, but team players who will thrive within your company culture.

A Rhythm for Accountability and Alignment

A key to scaling successfully, David shared, is creating predictable rituals and systems that keep teams aligned, motivated, and focused. He emphasized a weekly cadence that ensures clarity at every level:

Day	Meeting/Event	Purpose
Thursday	Dashboard Review Meeting	Leaders prep key metrics, assess progress, and ready for Friday’s review.
Friday	All-Hands Team Call	Celebrate wins, reinforce culture, and provide full transparency.
Monday	Leadership Huddle	Set weekly priorities and ensure alignment on goals and expectations.

 

“Dashboards on Thursday keep everything visible and honest. By Friday, everyone knows exactly where we stand, and we can celebrate the wins and tackle challenges head-on.”

These aren’t just routine check-ins—they are culture-building tools that keep teams connected and accountable, especially in distributed or hybrid environments.

Building Your Leadership Inner Circle

For key leadership hires—those reporting directly to you—David’s approach is clear: only hire from trusted networks (if you’ve been around long enough to have one).

These roles are too critical to gamble on. They require trust, proven track records, and alignment with your leadership style.

David’s inner circle is structured with complementary roles:

Role	Core Focus
Financial/Operational Lead	Oversees budgets, vendor management, and resource allocation
Delivery Lead	Drives execution and technical oversight
Strategic Connector	Bridges dev, product, and client relationships

 

“I need people who can handle hearing, ‘That sounds like a you problem,’ and step up to own it,” David emphasized.

This kind of trust and autonomy is essential for scalable leadership—and it frees you to focus on high-level strategy and vision.

Need help sourcing Salesforce leadership talent? Our network at The Salesforce Recruiter is built for this.

Final Takeaway: Lead with Clarity, Even in Ambiguity

One of David’s closing points on the podcast was a critical reminder: while ambiguity is unavoidable in complex Salesforce projects, great leaders are clear about that ambiguity.

“You can be absolutely transparent with your team: Here’s what we don’t know yet, and here’s what we expect you to do in the meantime.”

At The Salesforce Recruiter, we help organizations like yours build Salesforce teams that combine technical expertise with strong cultural alignment—setting you up for long-term success.

Ready to build a high-performing Salesforce team that scales the right way?

Let’s talk. Book a free strategy call and get tailored hiring insights based on your goals.