Your first 90 days in Sales Leadership (Or how to fix your sales quickly)

So, you've just stepped into a new role as a Sales Manager, Director, or VP in an early-stage startup. Exciting times! The beauty of this stage is the immense upside—you have the chance to leave your mark and build something meaningful. There's more room to innovate, especially when considering strategies like sales outsourcing in Europe or exploring how to expand your business to Europe.

But let's be real: resources are limited, and you can't afford too much trial and error. Your founders and CEOs—your bosses—are expecting fast results. If they've raised funds and aren't bootstrapped, their patience will be even thinner.

Here's a sobering thought: In the U.S., stats are coming out that most VPs of Sales don't survive a year at a company. In fact, like Jason Lemkin once said, 70% of first-time VPs of Sales in SaaS companies don't make it to their 12-month anniversary. There's also data that affirms that the average tenure for a seasoned executive at tech startups is about 17-19 months. Whether it's true or not, I've seen similar patterns in Europe.

Sales isn't an exact science, and that adds the challenge of managing expectations and perceptions. Trust me, your CEO will always think more could have been done, that better results were just within reach.

So, I've compiled a list I wish I had a few years back. It's especially useful if you own the sales function at your company. But even if you're an individual contributor, it's a solid checklist to understand the underlying levers of your job.

I advise going through this list within your first 90 days. Or, if you're already in the thick of it, revisit your current state to start fixing things on the go.

Objectives of This Checklist:

1. Quickly Assess the Maturity of the Company and the Sales Function
2. I've sat in countless meetings where clients say, "We need help, but we know what's wrong and how to fix it because we are the best." Don't rely on that. Assess, diagnose, then fix. If you fail following their diagnosis, you're probably fired. If you're a founder, you simply won't make it to the next level of growth.
3. Identify Gaps in Knowledge and Assets
4. I want to know if the messaging is figured out, the value proposition is clear, and if we know the niche we're targeting. Can we accurately describe their pain points? Do we have standardized messaging through scripts to allow for scale and real feedback loops?
5. Be Actionable
6. I don't gather info just to gather info. I don't want to say, "I can't produce the results you want because I'm lacking something." I want to talk about fixing issues and increasing our chances of success.

0. Foundational Information

• Do We Have a Detailed Customer Persona Document?
• Understanding your customer is foundational. Without a clear persona, your efforts in expanding your business to Europe or anywhere else will be misdirected.
• What Is the Reason for All of Our Clients to Have Purchased (In Their Own Words, Not Ours)?
• Direct feedback from clients tells you exactly what value they see in your product or service.
• Who Are the Different Personas Involved in the Deals?
• Identify the user, sponsor, project manager, champion, etc. Knowing who influences the deal helps tailor your approach.
• Are There Call and Demo Recordings I Can Listen To?
• These are gold mines for understanding client interactions and refining your messaging.
• What Are the Reasons for the Last Deals Lost?
• Learning from past failures prevents future ones.
• Who Are the Main Competitors?
• Knowing your competition is essential, especially if you're considering sales outsourcing or exploring sales outsourcing in Europe.
• What Are Our Unique Selling Points?
• What makes us uniquely different from ALL our competitors? Why are we the best and only option for clients to solve their problem?
• What Are the Specificities of Our Buyers?
• Consider company size, industry, trigger factors like fast-growing, declining, hiring, not hiring, etc.

Starting here gives you a solid understanding of the problem, the solution, and the transformation you offer. You gain insights into the environment in which you operate and current product shortcomings.

But don't just gather data internally—verify it with clients. Talk directly to them and listen to recordings to have first-hand information. Often, guesses are presented as truths. I've been told one thing about the market, only to find out the contrary. If you don't verify, you risk losing weeks or months you don't have.

Receiving first-hand emails from your colleagues is also a great way to get up to speed. Understand what is going on with the contacts, what they say, and how they phrase their problems.

Biggest Outcome: The possibility to reduce risk by quickly identifying the niche most likely to buy. Create positive momentum by narrowing down to one niche, with one solution and one offer. Once you hit diminishing returns, use the cash generated to try the next niche.

But beware of red flags:

• "We have all sorts of clients; anyone can buy our software."
• This is a recipe for wasted resources. Focus on your ideal customer.
• "Companies of any size have bought our software."
• But did they stay? How much are they paying? Is it sustainable versus the cost of acquisition and the targets set?
• "We want to go into multiple countries at once."
• Have you done it before? If not, how do we verify market-specific variables? If you're thinking about how to expand your business to Europe, it's crucial to tackle the best-chance markets first.

Ambition is great, but it needs to be prioritized. Look for patterns—success leaves clues. Which clients bring the most money? What are the commonalities? By going deep, you can start with the right niche and cut your time to results.

1. Sales Assets

• Do We Have Sales Demo Scripts?
• Make sure you have one per product.
• Do We Have Cold Call Scripts?
• Again, one per product.
• Is There an Objection Handling Manual?
• Make sure it's broken down by sales demo and cold call, and by product.
• Do We Have Case Studies of Transformation?
• Leverage these to drive more results, especially when considering how to outsource your sales department or when targeting new markets.
• Is There a Brochure or Supporting Materials to Send After Cold Calls and Others?

Sales assets tell us how repeatable the messaging is. If none of these assets exist, either they're in the heads of the founders, or they aren't figured out at all, meaning you start further back than you thought.

Outcome: The possibility to understand client stories, grasp the value of the product, and narrow down the messaging. The goal is to make the messaging repeatable and scalable, creating standards and repetition within the team. This allows for measurement, assessment, and improvement. Not having these assets leads to increased guesswork and too much reliance on individual brilliance.

There are two possibilities:

1. The Founders Have No Idea What Worked, but It Can Be Reverse Engineered
2. The Messaging Exists but Needs Refinement to Increase Chances of Success

Alternatively, there are no case studies or possibilities of getting them, which raises the question: why were you hired in the first place?

Without proof of successful transformation, acquiring more clients is extremely difficult. Sales, at its simplest, is understanding a client's pain and matching it with a successful client story. So, you might want to start by fixing this by interviewing existing clients to figure out if the "product that should sell itself because it is so good" is actually a fad or the best-kept secret you need to shout from the rooftops.

2. Sales Metrics

• Historical Closing Ratios
• You want to know these and separate them by market segment, product, geography, inbound versus outbound. Then compare them to benchmarks to understand what drives the business.
• Current Number of Meetings Per Week
• Outbound versus inbound.
• Current Pipeline Size in EUR
• Stages of Current Deals
• Current Revenue Objectives and Deadlines
• What is the worst-case scenario? The best-case scenario?
• Current Activity Level to Drive Intended Results
• Time Past Deals Took to Close
• From first touch to contract signature.
• Cash Collection Time After Closing

Once upon a time, a Head of Sales started his job thinking there was €5M in the pipeline ready to close with a €2M target. I was the poor chap who had to break the news: these were stale opportunities left there for months and years to show bigger results to investors.

The internal narrative was, "They might get back to us; it has happened in the past." Yeah, sure.

So, don't just look at dashboards. And if you don't have dashboards, you might want to fix that first.

You need to call the prospects and run a couple of questions to qualify them. It's not unusual to find opportunities that will not close because the previous team or the founders did not qualify their deals. That's perfectly okay—no harm done here. But you need to face the truth, see reality for what it is.

Because if your €5M pipeline is actually €500K, you need at least an extra €5.5M in the next X months. X being determined by your target deadline (like end of the year) minus the time to sell.

3. Sales Stack

• What CRM Is in Use, and Why Was It Chosen?
• The right CRM can significantly impact your efficiency, especially if you're considering sales outsourcing or expanding into new markets like Europe.
• What Call Platform Is in Use?
• Are calls recorded or not?
• What Tool Is Used for Reporting as a Single Source of Truth?
• Is There a Sales Engagement or Cold Emailing Platform in Use?
• What Tools Are Used to Get Prospect Data?
• What Tools Are Used to Get Direct Numbers?

I've worked with companies that had the wrong stack for the purpose pursued. Startups using CRMs built for big companies, or CRMs built for a different industry or strategy.

Price is never the main criteria. Unfortunately, too many companies choose their stack based on the cheapest option. There's a lack of visibility on upside/downside, lost productivity, and other criteria that should be senior to price until you've narrowed down to a few choices.

4. Sales Processes and Methodology

• What Is the Sales Process?
• Is it clearly defined and documented?
• Are Market Research Instructions Documented Somewhere for Each Persona?
• What Qualification Methodology Is in Use on Top of the Process?
• Frameworks like BANT (Budget, Authority, Need, Timeline) or MEDDICC can be invaluable.
• How Are Deals and Calls Documented?

I've worked with companies that did not have a sales process. I've also worked as a sales rep for a company where the sales process extended over 2-3 months, but the client buying cycle lasted 12 months on average.

But the worst is still not having any sales process at all. If you don't know the next steps you should take, your prospects won't know either.

Most companies don't have a market research document either. This leads to new reps calling people who will never close into accounts that are not great fits. It can be easily solved by creating a document that details what "great" looks like. Or you can externalize the market research completely and make it into a fully functional department. The latter is uncommon in internal sales teams and leads to inefficiencies.

On a more granular level, not seeing the reasons for losing deals or being able to pinpoint bottlenecks prevents you from making fast improvements to the right place in the pipeline. Same thing for cold calls and demos. Sales is like a team sport—you need to review plays to understand where you made the wrong move.

Adding qualifications to the deals ensures you spend resources on the right projects and set aside the others. This is usually the last step in improving things as it necessitates a high degree of understanding of your niche. The criteria are both objective with frameworks like BANT or MEDDICC and subjective with industry or product-specific criteria.

Remember, your goal in the first 90 days is to set a foundation for growth. Whether you're expanding into Europe, considering sales outsourcing, or refining your sales processes domestically, having a strategic plan is key.

If you have any questions on the content of this article or want to further the discussion, feel free to reach out.

P.S.: Need more tips on sales outsourcing, or scaling your business to Europe? Let's chat. Reach me at alex@profitbl.com.

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