And today, in the age of AI, this temptation to find a “superhero” hire is stronger than ever. Founders often believe that a new GTM leader armed with a magical AI tech stack can bypass the hard work of building a solid foundation. They hope for a shortcut.

But the truth is the opposite: AI doesn’t fix a broken GTM engine; it only accelerates it, in either direction. If your fundamentals are flawed, AI will just help you scale your mistakes faster.

This is why understanding the classic failure points for a new revenue leader is more critical now than ever. Let’s break down the five most common traps.

What does it happen in reality?

Low tenure.

“70% of SaaS First VP Sales don’t make it to 12 Months. It’s one of the most common, and also most devastating mishires in startups.” This well-known quote by Jason Lemkin is, remarkably, still very actual today.

Industry surveys consistently show that the average tenure for commercial leaders has fallen under 18 months for growth companies and it keeps on falling in both US and EU.

Especially in the European tech scene during the last boom cycle, it was common practice for promising startups to raise Seed or Series A rounds between 1 and 15 million € from Venture Capital firms and go straight away all in for hiring a superstar pedigreed VP: the Maradona or Michael Jordan of Sales VPs.

Real examples.

Below I’m bringing two typical examples of scaleups I’ve known from direct experience in 2 different continental Europe countries.

First scaleup: move “Maradona” from overseas 

CEO of B2B SaaS selling into Middle Market / Enterprise. Good product. Proven product-market fit. Raised more than 10 million in 2018. Hired and moved a “Maradona” VP Sales from UK (with family) soon after the VC round. Fired the same VP in less than a year, poor results and poor cultural fit were the stated reasons. VP was replaced with internal solution and it did not work neither. The company spent the following three years to recover through some layoff and a painful path to break-even. Now they are doing fine although the original unicorn dream is over.

Second scaleup: go for the big leagues, US and UK

CEO of Marketing and Media tech. Good and early mover product. Proven product-market fit. Raised A round of around 9M$ at the end of 2018. Built straight away offices in London and New York and hired “Maradona”. Fired “Maradona”, hired “Michael Jordan”. Fired “Michael Jordan”. They went in real trouble with Investors. The CEO was fired in 2020. The business is a “zombie” and never recovered.

These are not uncommon cases, is it so?

What are the consequences typically

• Founder dreams at high risk of failure.
• Founder dilution on the next rounds (if existing VCs decide to support).
• Equity valuation down for everyone.
• Hundreds of thousands € in management, operational and opportunity costs.
• Unhappy Investors, unhappy Founders, unhappy Employees.

Why is this happening?

Why does it happen? For one or more of the following reasons:

Bad TIMING. Hiring a Scaler When You Still Need a Builder

The two companies, like it happens to many, were not ready to push so hard. They were missing fundamental go-to-market “postures” in order to prepare the company to sustain an efficient growth.

Before hiring the “right” VP the Founders have got work of “Fundamentals” to do.

If you are not ready, you are not ready.

A good and experienced VP cannot be a shortcut. It does not work. Almost never.

The down-to-earth CEO of the new reality must set and own the basic “Pillars” of the revenue engine before hiring the “right” VP:

• Find a winning pitch choreography and consolidate an effective answer to the main sales objections.
• Build a straight-to-the-point product marketing toolkit.
• Don’t destroy value through prices that are “too-cheap” or at the opposite by raising barriers to initial adoption.
• Build and make the team execute a Playbook with a simple and solid process.
• Validate a basic funnel and conversion KPI’s.
• Get a few sales reps consistently on quota and a small SDR team getting good First Meetings in agenda.

A great VP knows how to improve everything, go into the details and accelerate revenue. She will, but it needs to be the right moment.

To set basic and healthy “postures” must be your job.

Unreasonable EXPECTATIONS. Demanding Revenue Before Predictability

You could also hire a “Maradona” VP if you are not ready, but then be wary of the possible expectations you can reasonably set.

Nine women cannot have a baby in one month

If you do not have a kind of revenue predictability yet, the expectation towards the VP should be set in terms of building that predictability.

Don’t expect to get delivered high-growth revenue. Unless your product has got some kind of magic and if yes, until when?.

Targets you should set instead:

• A funnel that works around specific use cases that get validation with specific ICPs (Ideal Customer Profiles).
• Consistent conversion metrics and a qualified pipeline of meetings and opportunities with solid criteria.
• Clear and measurable milestones to make progresses towards predictability.
• Alignment with the Board around the milestones.

It happens often, especially with junior VP hires, that the CEO just assigns a sales (or revenue) target to the VP without any rational and fact-based criteria.

Today, this often manifests as expecting a new CRO to deliver hockey-stick growth in one quarter simply by implementing a new set of AI tools.

Guess what happens most of the times.

Don’t do that.

Wrong PROFILE (Part 1). The Corporate Titan in a Startup Jungle

Would you let a trucker drive your spaceship? No you wouldn’t, right?

So, don’t hire Leaders that only worked in big corporations (Google, Amazon etc are big corporations now) and expect them to be superstar VPs in a supersonic scaleup of 50-100 employees growing 3 digits year on year.

Even if the person is really valid, it takes time to adjust.

It took more than 2 years to me when I moved from corporate world to startups.

Wrong PROFILE (Part 2). The Unproven Talent in the Driver’s Seat

Would you let someone drive your Ferrari as soon as they got the driving license?

It’s more and more common that promising startups with initial revenue traction (let’s say 500K-1,000 in ARR) raise 1 to 5 million € in VC capital and rush to hire as VP Sales a young Sales Pro with very limited or no real leadership experience. Most of the time the VP fails and burns out in a year or so.

Please don’t tell me that this is part of the risk associated to running a startup because it is not. This is a burst of talent and value.

Inexistent ONBOARDING. Expecting a Superhero to Work Alone

You don’t win the league hiring “Michael Jordan” and leaving him to do all the job just because he’s so expensive.

A revenue leader is a huge investment for a scaleup.

As CEO you should treat her onboarding as a top priority and learn how to do it properly. If it’s your first time you should ask for help.

How to manage the recruiting phase and the interviews. This is not like hiring an individual sales contributor or any other manager in IT, Product or Engineering.

Some of the key elements of the process you should master as Founder and CEO are:

• Setting the appropriate expectations.
• Uncovering the hidden truths.
• Building routines of work together.
• Building a win-win compensation scheme.

That’s just the start and it would help building a rewarding and positive relation.

CONCLUSIONS

So, is the modern CRO role broken? No.

What’s broken is the “superhero” mindset. The belief that one person, or one piece of technology, can be a shortcut around the foundational work of building a resilient Go-To-Market engine.

The one-size-fits-all, growth-at-all-costs approach imported from Silicon Valley boom times is a dangerous recipe, especially for European companies that need to prioritize capital efficiency.

The alternative is not to avoid hiring a leader. It’s to partner with a leader who is both a strategist and a hands-on operator. Someone who knows the difference between building and scaling. Someone who focuses on the “unsexy” fundamentals first (value proposition focus, process, playbook, people) to create a system that is sustainably super.

That’s the real job of a GTM leader. It’s not about being a superhero; it’s about building a team of them. And once you hire them, it’s crucial to maintain financial discipline, especially when it comes to managing the difference between real ARR and pilots, or what some are calling ERR vs. ARR. 

If you enjoyed this post, you might also like:

[A Founder Guide to Choosing the Right Help]

[The Fractional CRO: A Solution or Another Trap]

[The GTM Playbook Behind Woffu’s 9-Year SaaS Journey and Exit]

Subscribe to SaaSification for no-fluff GTM insights, frameworks, and real stories for AI-driven SaaS leaders.

The post The “Superhero CRO” Is a Myth: 5 Reasons Your Next GTM Leader Will Fail (and How to Ensure They Succeed) appeared first on Luigi Mallardo.

In B2B SaaS going upmarket (plus Partnership) is often the only way to keep on growing at a decent rate over time, especially past 3-5 million € in ARR. Whatever upmarket means for the specific business.

Many founders and operators still struggle with that idea and often they miss the execution of the most appropriate game plan.

I’ve seen many CEOs, VCs and startup operators having a “pure” Product-Led-Growth mentality for too long. They want the product to be cheap, horizontal and with zero or little sales support. The product needs to sell and serve by itself.

This is a nice concept but the issue is that this is an “exclusive” game for a few players. Sooner rather than later most B2B SaaS businesses realise that they need to embrace a bigger share of common sense.

Deciding to go upmarket doesn’t mean necessarily a drastic change or going just to big enterprises. It’s subjective and there is no one-size-fits-all recipe, although a few Principles stand out from the long list of factors that can influence the success or failure of an upmarket strategy.

Focus, Segmentation and Account Based Model

You need an accurate segmentation and a profound strategic work of focus and strict execution if you aim to go upmarket and grow average revenue per Account.

On an operational level you need to implement Account Based Models with Product Marketing, BDRs, Account Executives and Customer Success engines.

Marketing needs to be 100% aligned. Stop hiring inbound marketing experts promising the magic funnel. The funnel became dark in the last few years. There are 297 billion emails sent out for marketing purposes for 7 billion world inhabitants.

You need the right tech stack too. The industry has evolved exponentially in the last 3-5 years. Don’t go cheap on that!

“Deciding what not to do is as important as deciding what to do.” Steve Jobs

Hire people with experience and don’t stretch too much.

When the game gets serious you need people with proven experience.

If you give too much responsibility to junior folks and then things get difficult and there is too much pressure (which happens all the time in high-growth scaleups), it’s not going to work.

Don’t stretch too much. Not only hiring juniors and asking them to deliver like seniors. Also don’t expect that a salesperson who is good at selling 15K deals is also good at selling deals of 100K+ in ACV (Annual Contract Value). Or expanding Accounts from 100K to 1,000K in ARR.

Modern Leadership to go upmarket

At the right time you need a Revenue Leader who knows how to build a team and execute the game plan to move upmarket. You need a coach on the court. Not advisors or consultants. No shortcuts.

“The required profile of the sales LEADER has really changed to become more of a leadership profile. World-class managers today are defined not just by their ability to coach to the known, but by their ability to innovate around the unknown”. The Challenger Sale.

Review your Funnel and Playbook

Your funnel and sales playbook need to evolve as well.

For selling small and transactional deals the most used funnels in the tech industry have got “long necks” and “short legs” (quite dense at the top and very basic at the bottom), like the funnel below.

To get bigger deals you need a different type of funnel, a funnel with “long legs” given that it’s in middle and bottom of the funnel that most opportunities get stuck. That’s where you need more granularity and attention to detail.

An example of a proven funnel for deals above 50K in Annual Contract Value is below.

Review your pitch approach and focus on quantifiable outcomes for the customer.

Going upmarket means also an evolution of the way you communicate and what you communicate.

Sales cycles get longer, the (1) number of stakeholders you are in contact with in the same Account goes up and (2) you need to build a different narrative around (3) a sequence of touch points.

Talking about generic benefits and doing cold product demos it’s not as effective as with smaller deal sizes or the initial growth phase of the company.

Yes, of course you need to talk about your product BUT first of all show them what’s in it for the business. Don’t show just your product and how beautiful and usable it is.

Prospects want to be showed the products through real stories where they can see themselves reflected.

You should build teaching pitch choreographies to have an authentic conversation with your prospects about “Type B Benefits”, as very well conceptualised by the SPIN selling methodology more than 30 years ago.

How do you get your entire sales force to tailor their approach to each individual stakeholder’s most pressing needs?

Review your Customer Success formula

When you go upmarket your Customer Success approach may need a change. When you sell transactional deals or even deals up to 20-30K in ARR it may make sense to have two separate organisations: Sales handing over 100% a new Client to Customer Success.

Depending on how much upmarket you want to go, this will likely need to evolve. Selling and Servicing become a team efforts and Strategic Sellers (Strategic AEs) work together with Customer Success Champions (CSM), organised in Squads.

In such circumstances Customer Success should not be responsible for Upselling and Cross-Selling. Customers don’t need another Sales person. They need a Trusted Advisor with a different approach. This is not about selling 5 or 10K ARR. You need different people, a different CS funnel, even a different bonus scheme.

Complex topic. What am I missing here?

If you enjoyed this post, you will also like Game Plan for a Healthy Go-To-Market in B2B SaaS and Is the “classic” VP Sales model broken in mainland Europe? and SaaS Revenue Leaders. How to reduce the main risks in VC-backed startups.

Photo by fauxels in pexels.com

The post Game plan for going upmarket in B2B SaaS appeared first on Luigi Mallardo.