Questions every sales leader should ask before taking the job.
Too many sales leaders join a company and leave after 6 months. The question isn’t why it didn’t work, but why the risks weren’t clear earlier.
Good companies actually appreciate these questions. They show you care about outcomes, not just titles.
Below are the questions I’d never skip, based on a recent session at Pavilion GTM Leadership Accelerator School, with insights shared by Andrea Kayal.
1. Customer health & retention
Ask about:
Gross retention (how many revenue dollars stay by year end)
Logo retention
Net Revenue Retention (NRR)
If retention is weak, ask why. Persistent churn is usually a product problem.
If the product doesn’t meet customer needs, no customer success or account management will fix that.
2. Business health
Ask:
Growth target vs. actual (YoY, QoQ)
LTV / CAC
Payback period
Gross margin
Rule of 40
This tells you whether growth is sustainable or just expensive.
3. Booking targets & GTM mix
Ask:
What is the ACV (average contract value)?
Which GTM lanes contribute to bookings: inbound, outbound, partners?
How diversified is revenue today?
4. GTM diversification = capital question
If 80–90% of revenue comes from one channel, you’ll likely need to diversify.
Understand the cost of doing so and whether there is a budget for it.
Diversifying GTM is expensive. Building a new channel often means building a startup inside the startup.
If the company wants diversification, ask: How much capital is allocated?
When do they expect results from the new channel?
5. Sales cycle & pipeline reality
Ask:
Average sales cycle length
Pipeline coverage: how much of next quarter’s forecast already exists vs. still needs to be built. This tells you how hard the job really is.
6. Team & culture signals
Ask about:
Employee attrition (how many people leave the company over a year)
Which departments churn the most? Glassdoor rating (below ~4 is usually a signal, don’t let it be explained away)
If culture is broken, your job will be much harder.
These questions don’t make you “difficult.” They make you prepared.
And they significantly increase the odds that when you do take a role,
you can actually succeed in it.
Sadly, I've learned that lesson way too late.
It might sound like a stereotype, but I truly believed that "process can solve everything". Well, I am German so I guess this is fair to assume 🤔. It hurt more when I found out that it's actually counter productive in a lot of ways.
The struggle is: you never know what you don't know. When you are making your first steps as a commercial leader or heading a department, others expect you to know it all.
It feels lonely, comes with a lot of anxiety and some misbelief in yourself. In the end you can't know it all, and it's also not what should be expected by others or by yourself.
Last night we wrapped up the very first session of this season's Pavilion GTM Leadership Accelerator. All the messages I got afterwards are a clear testament to the above.
Here are three learnings you can use as a commercial leader yourself to make less mistakes than anyone before you:
1️⃣ It's ok not to know: The times are gone where you need to be the absolute authority in the room. As a leader it's your responsibility to excel at two things: First, lead with vision, context and clarity so everyone can be at their best. Second, compensate for your weaknesses in hiring or further education (see Pavilion University 🎓).
2️⃣ Be vulnerable: Share your struggles from your very own perspective. Help people understand where you stumbled in life, how you resolved difficult situations and what you gained from it. It does not only make you more approachable as a leader, but shows to everyone that we are all just people.
3️⃣ Facilitate community: Exactly like in Nadja's comment. So many people are going through the exact same experiences you are going through. Connect with a community where you find those peers, share with them and you will be surprised by the magic of "give to get" which creates incredible leaps in your personal development.
What did you recognize way too late?
🎉 First milestone unlocked with Pavilion!
Proud to have completed the GTM Leadership Accelerator Certificate – my first accomplishment with this amazing community.
One of the biggest reasons I chose to join Pavilion was the influence of my first GTM leader and the person who helped shape the CSM in me: André Bressel. His leadership made a lasting impact on my career, and having him as one of the standout lecturers in the course made the experience even more meaningful.
Pavilion isn't just a place to get best practices in GTM and CSM — it's a powerful peer community that keeps on giving:
✅ Real-world frameworks
✅ Thoughtful discussions
✅ Incredible people to learn and grow with
Big thanks to everyone involved. Onwards! 🚀
#GTM
#CustomerSuccess
#Leadership
#Pavilion
#LifelongLearning
Always a believer in continuous learning and sharpening my toolkit — proud to have completed the GTM Leadership Accelerator with Pavilion.
Leadership isn’t a destination; it’s a constant process of evolving, listening, and leveling up.
Grateful for the valuable insights and connections made during this journey, and looking forward to applying them in meaningful ways.
#Leadership
#GTM
#GrowthMindset
#Pavilion
I’m new to Pavilion and have just completed my first certification - the 8-week GTM Leadership Accelerator - and thought I'd share a few takeaways.
This course delivered real value and created a moment for me personally to reflect on the importance of carving out time to continue building skills, expanding perspective and strengthening one's network.
The program was well worth the time, but a few highlights that really stood out for me:
💡 Sam Jacobs' session on building a theory of enterprise value was a sharp, well-delivered reminder of the importance of not taking your eye off the ball and why sales and marketing exist in the first place.
💡 Stephanie Valenti's sessions on revenue modeling and forecasting delivered clear, practical frameworks that I will regularly return to (I've already watched them twice!).
🤝 A core part of the program is a weekly hour with a peer cohort, and these conversations added tremendous value. I’m grateful to Nadja Bennett, Klajdi Sallaku, Jamie Watters and Kirsten Aebersold for the thoughtful perspectives they brought.
Onward to 2026 - Happy New Year, Linkedin!
lnkd.in/guKBbFtx
🚀 Huge shoutout to Andrea Kayal for delivering a dynamic and empowering session in Pavilion ‘s GTM Accelerator course: “Managing Up - Working Smarter with Your CEO.” This class was packed with actionable insights and strategies that truly landed like a power punch to the chin! 🥊 👊🏻 Andrea’s approach brings a fresh perspective to the art of navigating the complex relationship between sales leaders and CEOs.
Here’s the left hook to the liver! 🥊
👉 Building a Bi-Directional Relationship with Your CEO: It’s not just about managing up, but cultivating a partnership that’s mutually fulfilling and strategic. You can’t thrive unless the relationship is nurtured in both directions.
👉 Set Yourself Up for Success from Day One: Andrea emphasized the importance of laying down the right foundations early on—whether it’s aligning on goals or understanding the CEO’s vision. This sets the tone for your trajectory.
👉 Foundations with Your Team and Execs: It’s not just about the CEO. Establishing clear expectations and fostering collaboration with both your immediate team and the executive team is crucial.
👉 Questions to Ask Before Accepting a Role: Know what you’re walking into. Andrea provided key questions to ask during the interview process to ensure the environment is set for your success.
💡 The takeaway that struck me the most? If you want a seat at the boardroom table, ask for it. Be proactive in defining your role and value from the start.
Andrea’s perspective is invaluable, and while I’m certainly not the authority on this topic, I hope this serves as an additional layer of insight as you think about your own path forward.
#GTMAccelerator
#Leadership
#ManagingUp
#CareerGrowth
#SalesLeadership
#Success
Well this is exciting!
I’ve been taking the GTM Leadership Accelerator course through Pavilion for the last 9 weeks, thanks to the learning & development budget we get at Genio
And I passed! 🎉
(Aced it, actually 😏)
The course was really well put together with some practical tips and takeaways from teachers like
👉🏼 Remco de Vries on Revenue Alignment
👉🏼Stephanie Valenti on Forecasting & Revenue Modeling
👉🏼Andrea Kayal on Managing Up to a CEO
👉🏼Sam Jacobs on Developing an Enterprise Theory and a deep dive on unit economics
…and so many more!
I love that our “Growth is a Mindset” value means I can invest in continuous learning 💜
#gtmleadership
#pavilioncertified
#growthisamindset
#gtmlearning
🎉 Excited to share that I’ve completed the GTM Leadership Accelerator with Pavilion!
Over 8 weeks, I had the chance to dive deep into business metrics, strategy, and effective communication with industry experts—and take a big step toward my leadership goals. Grateful for the learnings, and the opportunity to grow! 🚀
#growth
#Pavilion
If you're not learning, then you're falling behind.
Really enjoying the GTM Leadership Accelerator through Pavilion. We're 2 weeks in and I'm already filling up a notebook with actionable items that I can use.
I completed the Enterprise Sales School a few years ago at Pavilion and I've used those tools for myself and others ever since. I realize there are a ton of programs out there- but I've personally found the Pavilion courses- and the relationships that you build to be valuable. Happy to chat about my experience if you're curious.
Excited to announce that I’ve successfully completed the GTM Leadership Accelerator course with Pavilion. Thank you Assignar for the opportunity! The 8-week journey was filled with invaluable insights from top business leaders and educators in the go-to-market space.
I’m excited to bring these insights into action and continue driving impact. If anyone else has taken this program, I’d love to connect and share experiences!
Pavilion delivers again! An awesome course for any GTM leaders looking to level up their game. For me the biggest value add was the networking and the ability to share the learnings with peers from across the globe throughout the course.
Thanks to all the awesome moderators who generously shared their time and wisdom through the program Sam Jacobs André Bressel Stephanie Valenti Andrea Kayal Dustin Clinard Remco de Vries and Kiva Kolstein - we appreciate it!
The year has just started, and the first achievement is in. ✅
Completed the Pavilion GTM Leadership Accelerator - packed with insights and takeaways.
Surprisingly, I enjoyed the sessions about numbers and metrics more than the ones about people. On my way to applying it all in practice.
I'm really grateful to be a member of Pavilion. Their Revenue University is tremendous. Just enrolled for their GTM Leadership Accelerator course to strengthen my leadership and revenue strategy skill set.
I recently took some time to complete Pavilion's GTM Leadership Accelerator course. It was a great opportunity to measure myself and how I work against best-practice and learn from some leading SaaS practitioners.
While I was there, I also took the time to polish up on MEDDICC Fundamentals, something that's particularly relevant as we head into 2026 at LRN.
Every year the bar is set higher for what it takes to be successful. Clients expect higher standards, competition gets tougher and more crowded, the world changes in unexpected ways.
Grateful to have a successful 2025 in the books and with these recent learnings banked, I look forward to and feel ready for what 2026 brings.
Questions every sales leader should ask before taking the job.
Too many sales leaders join a company and leave after 6 months. The question isn’t why it didn’t work, but why the risks weren’t clear earlier.
Good companies actually appreciate these questions. They show you care about outcomes, not just titles.
Below are the questions I’d never skip, based on a recent session at Pavilion GTM Leadership Accelerator School, with insights shared by Andrea Kayal.
1. Customer health & retention
Ask about:
Gross retention (how many revenue dollars stay by year end)
Logo retention
Net Revenue Retention (NRR)
If retention is weak, ask why. Persistent churn is usually a product problem.
If the product doesn’t meet customer needs, no customer success or account management will fix that.
2. Business health
Ask:
Growth target vs. actual (YoY, QoQ)
LTV / CAC
Payback period
Gross margin
Rule of 40
This tells you whether growth is sustainable or just expensive.
3. Booking targets & GTM mix
Ask:
What is the ACV (average contract value)?
Which GTM lanes contribute to bookings: inbound, outbound, partners?
How diversified is revenue today?
4. GTM diversification = capital question
If 80–90% of revenue comes from one channel, you’ll likely need to diversify.
Understand the cost of doing so and whether there is a budget for it.
Diversifying GTM is expensive. Building a new channel often means building a startup inside the startup.
If the company wants diversification, ask: How much capital is allocated?
When do they expect results from the new channel?
5. Sales cycle & pipeline reality
Ask:
Average sales cycle length
Pipeline coverage: how much of next quarter’s forecast already exists vs. still needs to be built. This tells you how hard the job really is.
6. Team & culture signals
Ask about:
Employee attrition (how many people leave the company over a year)
Which departments churn the most? Glassdoor rating (below ~4 is usually a signal, don’t let it be explained away)
If culture is broken, your job will be much harder.
These questions don’t make you “difficult.” They make you prepared.
And they significantly increase the odds that when you do take a role,
you can actually succeed in it.
Sadly, I've learned that lesson way too late.
It might sound like a stereotype, but I truly believed that "process can solve everything". Well, I am German so I guess this is fair to assume 🤔. It hurt more when I found out that it's actually counter productive in a lot of ways.
The struggle is: you never know what you don't know. When you are making your first steps as a commercial leader or heading a department, others expect you to know it all.
It feels lonely, comes with a lot of anxiety and some misbelief in yourself. In the end you can't know it all, and it's also not what should be expected by others or by yourself.
Last night we wrapped up the very first session of this season's Pavilion GTM Leadership Accelerator. All the messages I got afterwards are a clear testament to the above.
Here are three learnings you can use as a commercial leader yourself to make less mistakes than anyone before you:
1️⃣ It's ok not to know: The times are gone where you need to be the absolute authority in the room. As a leader it's your responsibility to excel at two things: First, lead with vision, context and clarity so everyone can be at their best. Second, compensate for your weaknesses in hiring or further education (see Pavilion University 🎓).
2️⃣ Be vulnerable: Share your struggles from your very own perspective. Help people understand where you stumbled in life, how you resolved difficult situations and what you gained from it. It does not only make you more approachable as a leader, but shows to everyone that we are all just people.
3️⃣ Facilitate community: Exactly like in Nadja's comment. So many people are going through the exact same experiences you are going through. Connect with a community where you find those peers, share with them and you will be surprised by the magic of "give to get" which creates incredible leaps in your personal development.
What did you recognize way too late?
🎉 First milestone unlocked with Pavilion!
Proud to have completed the GTM Leadership Accelerator Certificate – my first accomplishment with this amazing community.
One of the biggest reasons I chose to join Pavilion was the influence of my first GTM leader and the person who helped shape the CSM in me: André Bressel. His leadership made a lasting impact on my career, and having him as one of the standout lecturers in the course made the experience even more meaningful.
Pavilion isn't just a place to get best practices in GTM and CSM — it's a powerful peer community that keeps on giving:
✅ Real-world frameworks
✅ Thoughtful discussions
✅ Incredible people to learn and grow with
Big thanks to everyone involved. Onwards! 🚀
#GTM
#CustomerSuccess
#Leadership
#Pavilion
#LifelongLearning

