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  • Writer's pictureJames Purvis

From Sales Rep to CRO: Zscaler's, Dali Rajic's Advice on Climbing the Sales Leadership Ladder

Whether you're a rep who was recently promoted into sales management or an existing sales leader who wants to further climb the ladder, you've looked into your bathroom mirror at any given point and asked yourself, "Am I ready? Can I really do this? What if I fail?" Imposter syndrome smothers us like a cold wet blanket in the middle of winter when you don't expect it. In order to escape, we frantically seek out approval from our peers, friends, and loved ones in hopes they can boost our ego so we can pick ourselves up and get back into the fight with the confidence that was temporarily lost.

We've all been there.

The truth is, we all have a lot learn and nobody has completely mastered the current role they're in. And they sure as hell haven't mastered the one they're striving to get. This discomfort is often what drives us. It's also what gets us down. A great way to get out of a slump or to stay on top is to continually educate ourselves. Advice not often shared in sales is how we should define the different layers of sales management and what strategies and actions we should be taking within each of these roles.

Someone who has come as close as it gets to mastering these layers is Zscaler's Dali Rajic.

Dali began his sales career as a rep at The Standard Register back in 1995, got his first sales leadership role 11 years later at Verint and starting cashing in on his success. He found his groove and climbed the ranks at BMC Software over the next 3 years and in 2012, Dali moved over to the hot startup App Dynamics as an Area Vice President. Here is where he really made a name for himself as he ascended all the way to the top as CRO and helped them achieve a $3.7B exit to Cisco. Since then, he took his CRO title over to Zscaler and now leads as a Chief Operating Officer.

It's safe to say, there is A TON we can learn from Mr. Rajic and this post is aimed to help us sellers shove that imposter syndrome aside for a minute and gain some useful knowledge as we investigate our next step in the sales leadership stairway.

Luckily for us, Dali joined the Revenue Builder Podcast hosted by five time CRO John McMahon and Force Management's John Kaplan and shared his guide to sales leadership success as we scale the different roles within the organization from first line manager to CRO.

Here are Dali's Best Practices to Consider and the Pitfalls to Avoid as You Move Up in the Sales Org:

First line management role

The one thing he felt he had to learn (there are many) but it would be accomplishing goals and objectives by working through others.

Best Practices:

  • Solve objectives through others: Dali calls this, "style flex." This is having the ability to work thru others without being demanding of things to get done.

    • As first line managers, we have tendency to "know the best path" since we were likely highly successful sales reps a short time ago. But it's important to remember that this was only the best path for you.

    • Build a team by mission, purpose and personal connection.

  • It's ok to be vulnerable: Just because you're in sales management now doesn't mean you know everything!

    • Dali presses that you should create a culture of mutual learning and become a sounding board for your team.

    • Admit that you don't have all the answers (which Dali knows is a hard thing to do). There are folks on your team who are better than you. Learn from your team.

    • Create a playbook by collecting all the experiences from your team and other teams to evolve the playbook.

Pitfall to Avoid:

  • Don't build "mini-clones": Not everyone is just like you. You end up pounding on people who are not like you and that creates a toxic culture.

“If you’re just chasing deals quarter in, quarter out, you’re going to burn people out." - Dali Rajic

Second line manager role

When you step into the second line role, it gets harder because it's not just individuals and you can't be everywhere at the same time. It's time to build that first step of General Manager skills.

Best Practices:

  • Be programatic: Things get harder in second line because it's not just individuals you have to understand and manage anymore. You have to be programatic because you can't scale yourself.

    • It's important to track progress and efficiencies because you want to maximize yield as much as possible. Note: There's only 62 real days for any given quarter.

  • Know your incremental value to the team:

    • Figure out how to connect to the ecosystem. Build partnerships that move the needle.

    • Find gaps without tripling down on rep inspection.

    • Help the first line manager understand the differentiation between their reps and accelerate their learning curve.

  • Ask other leaders for advice (and be naturally curious): Someone else is already doing it. Ask for their help - there's nothing wrong with that! This has always been a big part of Dali's playbook.

  • Ask the uncomfortable questions: Managing to risk with the deals, the individuals, and the team.

Pitfall to Avoid:

  • Avoid doing what the first line manager always does: A very common trap for second line leaders is asking the same questions the first line manger does. Reps won't know your value and it causes confusion.

“If you get the best people, and if you train and retain them with a strong sales process, the revenue will come. And if you understand how to drive that revenue programmatically, you can maximize how fast it comes and how big it gets.” - Dali Rajic

Third line manager role

You have to be thinking 3-4 quarters and working backwards. You are building out not just this fiscal year but the following.

Best Practices:

  • Operational cadence: You need to figure out how to maximize the existing business as well as create new businesses. Dali believes it's key to helping the Sales Managers and Directors to recruit, retain, and drive the number and build a rhythm.

  • Connect with the product team: Determine what capabilities to surface up that can bring home more customers.

  • Build the next phase of the organization: Do this while keeping a pulse on the entire org.

    • Figure out the ratios of the team in an efficient manner.

  • Don't lose touch: Create Advisory groups with SEs, Customer Success, Reps, etc and get feedback from the ground.

    • Do it outside the team bubble and compare metrics. What's the pulse and why?

    • Leverage the brilliant minds of the extended team.

Pitfall to Avoid:

  • Chasing deals. You're no longer chasing the quarter or quarter + 1.

"Look at the overall business and ecosystem that we should be partnering with. Start thinking like an executive." - Dali Rajic

Fourth line manager role

This is the time to start "Thinking like an executive."

Best Practices:

  • "Think like an executive": You have to start thinking like a CRO - understand the "Lead to Cash"journey.

    • You can do this by becoming intimate with the marketing and finance team. It's one unit for your GTM org.

  • How to get maximum yield:

    • Where are you getting the most deals from the campaigns? It's time to run analysis on where investments are producing the largest returns. What profiles? Regions? Models?

    • Understanding each region and how marketing aligns in the overall business plan is crucial. It's all about having a clear map of where to spend your resources. Dali says it's like an investment portfolio to maximize yield and sales productivity. It's investments if the far future.

    • Determining timing on when to become account focused and segmentation focused is a difficult but a critical decision to make.

Pitfall to Avoid:

  • Thinking in terms of quarters. It's time to think 2-3 years ahead.

“I’m always wondering why and how something is the way it is, and don’t just accept the status quo.” - Dali Rajic


Building a powerful squad of lieutenants and a well-oiled revenue operation.

Best Practices:

  • Build a strong team of lieutenants: Dali stresses that these folks need to have entrepreneurial minds.

    • Make bets on people but don't overstretch them. This is often difficult because everybody thinks they're more ready than they actually are.

    • Have a goal of getting people to realize you have their best interest in mind. This will help others get to where they want to go and they will never leave you.

    • Ability to recognize that if you have a consistent problem in a certain area, it's likely that it's the leader that's the issue.

  • Create a revenue ops team that is strong: He thinks of revenue ops as "eyes in the sky" for key insights you can utilize. These folks are not just collecting data but interpreting it.

    • You should create a financial model that if you don't hit, where can I pull back.

Pitfall to Avoid:

  • Believing there is time to inspect everything. There's not. Instead, build 3 year plan and work backwards for key metrics on a quarterly basis.

“We provide a platform and framework, as well as playbooks that enable salespeople to reach their full potential, with the patient guidance of leadership.” - Dali Rajic


Dali will tell you, a sales leader doesn’t have all the answers. It's okay to be vulnerable because getting promoted doesn't mean you know everything. That's a trap. There is a ton of talent on your team so leverage that by creating a culture of mutual learning allowing for the frequent exchange of ideas, weighing them, and figure out how to put them into action. You are there to become a sounding board for the team and learn, evolve your thinking, and start adding incremental value.

Bye, bye imposter syndrome. You are good enough and right where you should be.



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