How I fixed my “broken rung” and everything I learned along the way
I’d been trying to finagle my way into management since 2018. I was super vocal about what I wanted, but the cards never aligned when I made internal asks. Then, this Spring, I left my full-time job to pursue a Sales Manager position full-time…
And, let me tell you: I tried EVERYTHING. 😃
At first, I was looking at Account Executive roles at other companies. I had spoken to the CEO and Head of Sales at my company about getting into Sales Management. They gave me a timeline of 18 months. And, of course, as a startup, their plans changed.
This was the third time I tried to get promoted internally at a company. And it wasn’t working. I was ready to take my business elsewhere where there might be a clearer path-to-promotion. I didn’t think it was possible to switch companies and get a promotion at the same time.
While I was in those AE processes, another recruiter reached out to me about a Sales Manager role. I couldn’t believe it, so I double-checked…
“Hi Nicole! I’m interested, but I want to make sure this message wasn’t sent to me by mistake. I have 7+ years as a full-cycle account executive. I have been trying to break into sales management since 2018. Do you think your Director of Sales would actually consider my profile?”
She responded:
“The short answer is yes, as long you can flex some muscle when it comes to coaching, mentoring, or training others. He’s willing to consider a strong Senior to leverage into this manager role.”
I never thought anyone would consider me for a Sales Manager role at another company. It was both a promotion and a company change, and that seldom happens. So I had never tried. But here was this recruiter willing to give me a chance.
Unfortunately, I made it all the way to the end of the process, but I didn’t get that job. But that experience planted a seed in my head and changed my perspective…
Lesson #1: Getting a manager role at another company is 100% possible.
So then I worked with my leadership at my previous company to create an off-boarding plan. They didn’t have the role I wanted as soon as I was expecting. They knew I was looking and they had to plan for pipeline coverage for their small company. My employment ended on a positive note and I went along my merry way.
Since I wasn’t going to have my 1:1s with my manager anymore, I reached out to Colleen Manning. She’s a Sales & Career Coach I knew from the Women In Sales scene in Boston. I signed up to work with her for 6 weeks. I felt that meeting with someone regularly would help keep me accountable. And her experience would help me see things I couldn’t see on my own.
One of the first things I did after that was back out of the other Account Executive interviews. I was mid-process with some other companies. So I let them know I was rescinding to pursue a Sales Manager role.
What’s nuts is that two of the companies came back to me and said they’d interview me for their open Sales Manager roles! 🐿
I told both of the recruiters at these companies early on about my interest in leadership. But they didn’t recommend I interview for a manager role instead. Instead, they sold me on their career pathing methodologies. When I was able to impress the hiring managers, I became a worthy candidate for a Sales Manager position.
I learned that recruiters are qualifying if you’re worth the Hiring Managers time. The Hiring Manager is the one who decides if you can do the job. Don’t let a Recruiter tell you that you can’t do the job. It’s like letting the front desk tell you that the entire company is not interested in buying your tool. They don’t know that, lol!
Lesson #2: Say what you gotta say to get past the Gatekeeper and then prove yourself to the Decision Maker.
I took one of the companies up on their offer because one of the companies was giving me some red flags. I couldn’t put it into words. It was just a feeling.
Lesson #3: Always listen to your red flags! 🚩🚩🚩
What was cool about my next interview process was that they gave me all the questions ahead of time:
- What metrics do you focus on as a sales leader?
- How do you coach each rep, your team, and partner with other leaders?
- How do you develop yourself?
- Hiring, Firing, & Performance Management
- How do your Forecast and coach around Pipeline Management?
- How would you establish and create Team Culture?
So little smart-aleck me took those questions to my network. I reached out to Sales Managers and asked for 30 minute informational interviews. My plan was to combine answers and use the best ones in my interview.
Hey Michelle! How are you? I’m reaching out because I’m actually interviewing for a Sales Manager role, and I have an ask! I know it’s short notice, but would you mind if we met for ~30 min tomorrow, Friday, or Monday? I’d love to pick your brain on what your day-to-day looks like? I understand if there’s no way you can make that work. Thank you either way! :)
I killed it in my interviews. But the feedback I got was that I spoke very theoretically. The hiring manager wanted to know how I was going to do everything. She asked me to make a 30/60/90.
I put a lot of thought into it. I created a specific plan based on my notes about the team’s biggest challenges. Colleen gave me some 30/60/90 examples. I referenced my learnings from reading “The Making of a Manager” by Julie Zhuo. And I also included some ideas from a Sales Impact Academy class. I was taking “Data-Driven AE Management.” I got access to this class through a kind and helpful recruiter, a connection of Colleen.
Then, I killed it on the 30/60/90 too! The feedback I got was that I may try to do too much in my first 90 days. Good to know…
And after many weeks of interviews, I didn’t end up getting that job either. They changed their headcount plans for that role. The timing was off.
But making the 30/60/90 itself was a game-changer for my interviews going forward. Now, I didn’t just know what to say, but I could explain how to do it. I felt like I knew exactly how to do the job I was interviewing for.
Lesson #4: Making a 30/60/90 for your dream role is a great way to conceptualize your strategy. And prove to a hiring manager that you have one.
I was reading a lot and attending a ton of webinars. My favorites are from Peter Kazanjy with Modern Sales Pros and Atrium. Because he’s a dynamic presenter and you always get to learn Sales Math!
All this while, I was reaching out to Sales Leaders I knew on LinkedIn, telling them about my mission:
Reaching out bc I’m currently on the prowl for a Sales Manager role. I don’t have official experience managing. But I’ve led many ERGs, been reading a lot of books, and I’m working with a sales coach. I’ve been a full cycle AE for 7+ years and really looking to get out of my comfort zone and into my growth zone. If you see any SMB Sales Manager roles in your network, would you please let me know?
I was targeting SMB Sales Manager roles at Series B or Series C startups with 100+ employees. This was advice given to me from my former manager. It would be hard for a Hiring Manager to hire an external Senior AE for an Enterprise Sales Manager role. They likely have a lot of ambitious AEs in-house who would gladly take on the responsibility. Optics-wise, it’s a bad look.
But many times, SMB AEs are pretty green at Sales, so I at least had 7 years of experience on them to earn their respect.
Anyway, reaching out to Sales Leaders in my network led to a plethora of other opportunities! One LinkedIn-famous Sales Leader connected me to another and I got to interview with him. He loved me and would have hired me, but his boss was super skeptical. SMB is that company’s biggest segment, and I wouldn’t have trusted a new manager for that role either. I don’t blame him.
Another Sales Leader I reached out to told me to immediately sign up for #GirlsClub. So I did.
#GirlsClub, if you don’t know, is a Sales Management Trainee program by the people who made Factor 8. It used to just be Factor 8, but they noticed not enough women were signing up. So they rebranded and added a whole pillar on Confidence-Building. I got in with a DEIB Scholarship to get 6 whole months of Sales Management training!
Adding #GirlsClub and my Sales Impact Academy (SIA) Certification to my resumé felt like a big win!
Along with getting into these programs, I also got into their Slack Channels. Which reminded me that I had invites to other Slack channels deep within my Gmail somewhere. So I logged in to those too and introduced myself.
Hey Folks! Anyone know of a company or sales leader who might be willing to take on a Senior AE for a Sales Management position? I’m Nirvanna Lildharrie, a full-cycle AE with 7+ years experience. I’m hoping to transition into Sales Management. I’m taking the Data-Driven AE Management Course with SIA. And I’m also enrolled in #GirlsClub Sales Leadership Program. Happy to provide a full cv. Thanks everyone!!!
Aside from #GirlsClub and SIA, I rejoined Sales For The Culture, Ladies Get Paid, Remote POC, and She+ Geeks Out. I figured, I have to tell these people what I’m looking for so they can think of me for opportunities. If you don’t ask, the answer is always No.
I was looking for more… On LinkedIn, I found an article called “Sales Experts & Communities to Follow in 2022.” I followed and added everyone and group on that list. Scott Ingram reached out to me:
Thanks for reaching out to connect Nirvanna. Just peaked at your profile. Looks like you might have some amazing insights to bring to our Daily Sales Tips podcast, if that’s of interest? My wife is also a Tufts alum. Go Jumbo’s!
So I made a Daily Sales Tip!
Then, Christian Parra reached out to me on behalf of Marcus Chan. We met and he shared a webinar with me that had an important lesson:
Lesson #5: To get any job, you need to convince the hiring manager that the Return on hiring you exceeds the Risk.
Marcus Chan’s words.
And then, Cynthia Barnes, who was on the top Sales Experts list, accepted my connection. I realized she was in Raleigh and asked if she wanted to meet for coffee. She is one of the friendliest, warmest people I know, so it makes sense now that she said yes.
Over coffee, I told her my story and she told me hers. I learned about her organization, National Association of Women Sales Professionals (NAWSP). I shared that I had experience running an events-based ERG called “She Makes Sense.” Then, she asked me if I would help build the women in sales community in Raleigh as Chapter President.
How could I say no??
It was also another big facelift for my resume and LinkedIn profile. I took a new headshot. I updated my LinkedIn Headline to say “Saas Sales Leader.” And per Cynthia’s advice, I started a daily content strategy on LinkedIn.
Through NAWSP, I met a lot of amazing Saleswomen who all wanted to help me in my search. I had a call with Cherilynn Castleman and talked to her about how I was on a mission to “fix my broken rung.”
“The Broken Rung” is a term coined by McKinsey in their Women In The Workplace study. What prevents women from leadership roles is actually a Broken Rung, not a Glass Ceiling. The hardest promotion for a woman to get is from Individual Contributor to Manager. After that, all the other promotions are way easier.
This was evident in all the above-the-line women I met in my interviews. Some of these women were AEs for 15 years, then they became a manager for 1–2 years. And then, all the sudden, Zoomed to the top as a Director or VP or SVP.
Now, I always like to be accountable for my own career. but learning about the Broken Rung got me thinking that maybe this was much, much bigger than me.
Cherilynn was super intrigued. And she asked me to do a LinkedIn Live with her. From her perspective, it would give me more visibility to help me with my job hunt. I appreciated her help so much! Little did we know, our LinkedIn Live about the Broken Rung was about to have a happy ending…
As I was job hunting, I had been through three whole cycles of interviews with no success. So I decided to widen my scope a bit.
At first, I was gung-ho about being a Sales Manager and I wasn’t going to settle for anything else. Then I became open to SDR or BDR Manager roles too. That got me some more interviews…
I also wasn’t super into being a player-coach for a very early-stage startup. I wanted some true management experience. Not building a GTM strategy from the ground up. But then I caved and started taking those interviews too. Because why not?
I also applied for Sales Enablement and Sales Trainer jobs. Which is what led me to become a part-time Tech Sales Instructor with Skillz Academy. It’s a bootcamp that helps underrepresented candidates get placed in Tech Sales jobs. Many of my interviewers were looking for a strong coach for their team. I figured this was a great way to get that experience!
After another big round of rejections, I started thinking: “Well, the world’s opening up. And I moved to Raleigh. I guess I’d take an AE role in Raleigh, go into the office, and use my dazzling in-office presence to get promoted fast!”
So I even applied to individual contributor roles that were local.
My resumé highlighted how I helped new teammates with onboarding at my last company. On one of my phone screens, a recruiter said, “It looks like you had some Team Lead experience too.”
“Team Lead!” I thought. And then I started searching and applying for Team Lead roles as well.
And that’s when I found the role that I ended up getting.
Every single interview in this process, I felt like I was getting up on my soapbox and giving my best dog and pony show. It was exhausting! But thankfully, I only had to do it for two months.
Finally, someone took a chance on me! And I start my new role on Monday :)
This whole entire process has been an adventure of a lifetime. There are many people I want to and will thank. But most of all, I want to thank myself.
I haven’t stopped working one day since I left my job. I had the self-discipline to learn new things. I had the bravery to put myself out there over and over. I had the grit to keep trying after every rejection. I had the stamina and resilience to not give up on myself. With both hands on my own heart, I feel deep appreciation for how I handled myself through this journey.
I’m proud of me! 😊
And, best of all, now I know how to help you do it too!
If you’re going through this journey and trying to fix your broken rung, I’m here to tell you it’s possible. Your success is in your own hands.
Don’t take No for an answer.
Don’t listen to people when they tell you that you Can’t.
Don’t stop believing in YOU.
