There’s no single path to the top in Sales. In some ways, it’s kind of like selling deals — you have playbooks and guides on how to win, but at each step of a deal, you have to ask the right questions and pick a next move that’s specific to that deal.
So I can’t offer a paint-by-numbers guide or a single specific approach. But what I can do is give you real-world guidance to move to the next stage of your career, and actionable tips on maximizing your opportunity.
Sure, I didn’t actually start in sales and work directly up that path. But what I have done is promote lots of people from BDR to AE, from AE to Team Leader, from Directors to VPs… you get the picture. I know what it takes to move up in the ranks.
So how do you begin the long journey to become a CRO? Let’s look at the roadmap:
- Picture Your Ultimate Goal
- Individual Contributor to Team Leader/Manager
- Team Manager to Director
- Director to VP
- VP to CRO
- Make Your Own Luck
Picture Your Ultimate Goal
Unless you’re already a VP, chances are that CRO is not the next step in your career, and thankfully, this guide isn’t just about that! Instead, it’s about advancing to the next step of your career. And it’s outlined in a way to help no matter where you’re starting.
And you don’t necessarily need to make CRO your ultimate goal either. You may decide that you really like being a VP of Sales and want to keep doing that role at a larger and larger scale, or at new companies. Or you may feel that CRO is just a stepping stone to becoming a CEO.
What matters most is starting with a picture of where you are today and where you want to go next. And it’s useful to have a broader roadmap that shows what future steps could look like too. And these are exactly what we’ll cover here.
Individual Contributor to Team Leader/Manager
In terms of skill expansion, this may be the toughest move to make.
Because it requires a fundamental shift in skills and thinking.
As an individual, almost all your metrics have to do with your individual performance. So, those who succeed in these roles are people who are great at focusing on what they need to do to succeed individually — shielding their time to maximize results and creating massive energy, drive, and focus in their personal day-to-day activities.
This not only works, it’s required… at least to some degree. You can’t hit your numbers consistently if you don’t put some serious discipline and focus on yourself.
Moving from an individual AE, AM, or CSM to a Team Leader role, on the other hand, requires something totally different. It requires focusing on and coaching others. It requires spending your whole day thinking about everyone except yourself.
Be sure you want to manage
If you’re an SDR/BDR, you have a very important decision to make before you start on your journey. Do you want to become an AE, and move up the path of owning deal revenue, or do you want to become a Team Leader or Director of SDR/BDR teams?
Both are valid, but often a company has fewer roles as leader of these teams. And many people decide they want to be directly responsible for closing the sale. So another individual contributor role — the AE role — becomes an intermediate step.
Once you’re ready to move to the Team Leader role, whenever that is, the obvious skill that’s required is that of coaching and helping others. Ask yourself if you really want this, because some people realize they actually don’t.
Managing a bunch of people has rewards, but people management carries with it huge challenges.
On top of that, you have far less control. When it’s just yourself, you do whatever you want and need to achieve your goals. When it’s others, you have to influence them and motivate them (yes, you can try to command and control them, but if that’s your cup of tea, then you need to get a time machine and go back to the 50s because that’s not how modern leadership works).
Many people think they want to be a Team Leader, but then realize that they would rather move up to increasingly larger enterprise sales. You can make a ton of coin doing that as well, and without having to manage people.
If money is your main motivator for moving up, take a look at some of those positions targeting large enterprise accounts and the OTE that can come with them. Be honest with yourself about which path fits you better.
What you need to succeed
Now, presuming you’re still excited about managing and leading teams after you’ve given it some hard thought, there are several ways you can stand out from the crowd and demonstrate your leadership potential to management.
The main thing is to show some leadership… anyplace. You don’t have to have a leader title to be a leader. You just need to act like one, and there are tons of ways to do it. You could set up informal lunch-and-learns, you could compile valuable insights and share them with management, you can offer to be a mentor to some others, etc.
Alex Mackenzie, Head of Mid-Market Sales at Klaviyo, had this to say about how he made this move:
“I led a Monday 6 PM ‘Ask Me Anything Session’ where I would dissect deals with other reps and help with their plan of attack. When it came time to talk about my ability to coach, I already had several people in the organization willing to vouch with real-life stories of how I helped them solve problems and get deals done.“
By the way, if you’re not excelling on your individual goals, put energy into that first. You won’t have a lot of credibility to lead others if you can’t demonstrate success yourself.
If you’re knocking it out of the park and people see you on the top of the leaderboard, they will naturally want to follow and learn from you. You just need to start offering that leadership.
If you demonstrate leadership and your company is growing, you’re likely to be noticed by management and be chosen for a Team Leader role. Even if your company isn’t growing super fast, you may still get rotated into one of these roles.
If you find your company isn’t growing and won’t be in the near future), then you may want to put your focus on finding a new company. Be thoughtful before you make this jump, though. You’ll have to start all over again at that new company — build pipeline from zero, build trust from scratch, etc. So, be sure that’s something you’re willing to do.
Team Manager to Director
The biggest difference between a Team Manager role and a Director role is that a director typically is in charge of a functional block of the company.
What does this mean?
It’s basically some defined section of your Go-to-Market — it could be owning a specific geography, a market segment (e.g., mid-market), a product line, etc.
Typically a team manager is focused on driving operational and executional performance from that team, and while they should be involved with setting the strategy for an overall functional block, that’s not their main job.
On the other hand, a Director is responsible for the strategy, planning, and results of that functional block.
What you need to succeed
There are basically three things you need to focus on to make this move happen:
- Excelling in your current role (your team is performing really well)
- Demonstrating the skills needed to move to the next level
- Creating or finding an opening you can fill
Excelling in your current role
There are tons of great resources on the Sales Hacker site to help you with the first, so we won’t get into all of those here. But make sure you avail yourself of those resources (there are also some great resources for the next-level skill sets too).
The community is also a great place to get plugged into if you have any questions! You can check it out and join here.
Demonstrating the skill you need
To hit the second requirement you need to demonstrate your ability to lead strategy and planning for a functional block.
And again, the way to do this is to show leadership you can do this before you actually get the title. It’s about finding ways to add real value to the company that demonstrates the next level skills.
For example, you could develop insight into a particular market segment where there’s more opportunity.
Some of the ideas mentioned in the prior section (e.g., setting up a lunch-and-learn) also work here, but you’ll need to adapt them to demonstrate the broader skill and thought-leadership around a bigger functional block — it could be about a particular vertical, an international market, improving sales of a newly launched (or to-be-launched) product.
Whatever it is, it should go beyond the operational performance of your team.
Creating or finding an opening
Item number three on the list is where it starts to get tricky, and actually, this gets more and more challenging the further you move up in your career.
Similar to the prior move, if your company is in a high-growth mode, that’s going to help you. In that case, your company may be expanding to additional markets, and you could land a spot leading one of those. Alternatively, you may be able to propose a new market as well.
But what if your company isn’t growing quickly?
Well, if you can identify a market or opportunity that could be a growth area, you might still be able to create an opportunity.
As a top-performing team leader, you will have developed a keen sense for when prospects buy and when they don’t. You could use this insight to identify a growth area, bring it to management’s attention, and position yourself to lead sales for the new area.
Of course, there’s risk and uncertainty in any new venture, so it’s something you should prepare for and develop some options for yourself.
The alternative again is to look for a role outside of your current company.
If you’re looking to jump up a level, your best chance will be either to find a company that’s a bit smaller than your current company but is growing quickly. You can position yourself for that next level position because you’ve already led a team that size. And if the company is growing fast, the scope of your role is likely to grow as well.
Director to VP
Organizations typically view a VP-level role as an executive, while they may view the Director-level role as mid-management. The question they ask is whether this person is ready to be a member of the executive team.
But what does it mean to be an executive? What are the requirements?
What you need to succeed
There are several key things that most companies look for in their executives:
- Is this person thoughtful about the overall strategy of the company?
- Can this person contribute to the overall executive team discussion — not just a functional area?
- How does this person lead?
- What kind of cross-functional relationships does this person develop?
- Does this person help foster and develop our culture?
This list varies from company to company, but most good companies hold a pretty high bar for executives to meet. The items mentioned above are typically the core requirements.
Mark Roberge had this to say about how he made the choice to promote a person to VP of International at HubSpot:
“We were looking to expand internationally, and I really needed someone to lead the effort as VP of International.
This was a tricky promotion as I needed someone that thought strategically, hired well, and ran a disciplined sales methodology, as I looked for in all of my VPs. However, they would also drive the culture much more so than any other VP in our company because of the physical distance and the less frequent exposure to our North American headquarters.
I needed a higher form of leadership to ensure success in that office.“
Finding an opening
As we get into the discussions about these higher-level career moves — including both the to CRO, the biggest challenge comes around whether your current company will have an opening for that next level role or not.
Startups will generally only have one VP of Sales, so getting a VP Sales opportunity requires either for that person to move on or for the company to split up the responsibility as the company grows.
For example, they may hire a VP of International as they expand. This typically only happens after a company has grown beyond the early startup stage, though.
Most CEOs will not want to have multiple VPs of Sales reporting to them — or at least not for the long term. They may do this for a short period of time, but they will really want to consolidate this under an SVP of Sales or a CRO position. That way, the CEO is free to lead more broadly across the entire company.
If your company is in the process of hiring a CRO or SVP of Sales, then this may be an ideal time to jump up to a VP Sales opportunity at your current company.
Get to know the incoming SVP/CRO, and develop a relationship, but don’t come across as purely ambitious. You don’t want it to seem like your only motivation is to land a new role.
Engage and show leadership you’re capable the way we talked about above.
What if there’s no opportunity?
So, what if these things don’t apply to your current company? If there’s no opportunity to move to VP at your current company, you’ll need to keep an eye out for outside opportunities.
It’s best not to rush into this. In most cases, you’ll be able to land a better VP slot if you take your time and have a longer track record of success as a Director. This is particularly true if you have that track record at a successful company.
If this isn’t the case, you may want to take another Director slot at a successful high growth company and do that role for another 3-5 years to continue gaining experience and build your network.
While nothing is guaranteed, the stronger your record is as a Director, the better choices you’ll have in picking your ideal VP role, instead of just taking the one you can get.
Keep in mind that the failure rate for startups is high, so you want to be able to be choosy.
VP to CRO
On occasion, I’ve seen small companies call their head of sales CRO, even when the role is exclusively focused on running a smallish sales team. This usually happens because the company is either in a rapid growth stage and is planning to scale quickly, or because they need to make the title be CRO to attract the person they are trying to recruit into the role.
If that’s the case, the criteria for landing this role is pretty similar to the VP Sales role that we spoke about above.
However, in most cases, the CRO role is much broader. This breadth usually falls into two buckets:
Either a large scale (likely global) sales role with multiple VPs reporting in, or a role that includes functions in addition to Sales — e.g., Customer Success and other functions such as Customer Operations, Customer Care, Alliances, and Marketing.
What you need to succeed
There’s no doubt that getting to the next level requires exceptional performance in your current role, as well as advanced development of the skills we’ve discussed, but these are just table stakes.
If you’re in a hyper-growth company and have continued to demonstrate the ability to scale and succeed, the company may end up needing a CRO, and you may be the one the company chooses. But if this opportunity doesn’t arise, you’ll end up finding your CRO role in a new company.
To land one of these roles requires strong industry relationships developed over the course of multiple positions of increasing responsibility. These include relationships with Board Members, CEOs who may have been your customers in the past, Executive Recruiters, PE and VC firms, etc.
Tapping into this network will not only help you find that next opportunity, it will help you land it.
Make Your Own Luck
The path to the top often has many twists and turns, and you may even decide at some point that you’re happy with a specific level and would rather repeat that role at other successful companies than push for the next role.
At other points, you may decide to take a step back to go forward. This is perfectly fine, and it’s important to approach those opportunities with as much gusto as any other role.
Ultimately, the thing to keep in mind is that the path to progress doesn’t come just from doing your job well — that is a requirement, but that alone won’t necessarily get you there.
Getting to the next level requires both excellence at your current role and a fair share of luck.
But even that is not totally out of your control. There’s the old saying, “the harder I work, the luckier, I get.” There’s actually a great TED talk about this by Tina Seelig, a professor at Stanford University.
The good news is that if you’re willing to work hard, develop your skills, get mentorship (even senior leaders can get mentorship), and build strong relationships both in and out of your company, there is no limit to how far you can go.
This was a great read @shamsao! Thank you for sharing your thoughts.