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Founder-led sales isn’t easy, so here are ten actionable tips to help you transform your sales strategy.
1. Prepare for every call
Even if you’ve received a warm introduction to someone, preparing as much as possible before every call is vital. Starting with macro industry-specific trends and company-specific information to prospect-specific insight, there is a lot that you can glean from publicly available information.
All too often, sales calls turn into relaying some “news” back to the prospect and some embarrassing flattery. For example, congratulating someone on their promotion or their speaking at an event. This doesn’t always work, and doing just this is insufficient as well.
You have to go beyond the news if you intend to connect the dots and come up with a hypothesis for why the prospect might care about the problem you are solving.
Let’s say that the company you are prospecting raised a Series C recently. Knowing that alone is not as helpful as it is when combined with key new hires they’ve made, any prominent products they launched recently, challenges that their execs might have shared in recent podcasts or conferences, and so on.
When you show up to the first call with a prospect, it will make a big difference when you truly understand and see the world from their standpoint.
2. Refine your listening skills
When I used to join sales calls, the best-performing sales representatives would always have a more realistic expectation of how likely a deal might move forward and in what timeline. The rest usually had “happy ears”–being more optimistic about the prospects than what the client suggested.
According to research, humans are wired to be poor listeners by design! Turns out we can process 400-500 words per minute but most humans can only speak at the rate of 125 to 150 words per minute. This huge discrepancy explains why our mind often wanders in conversations or leads us to multitask or worse–we tend to think about how to respond or what to say next even when the other person hasn’t even finished talking. This is absolutely detrimental to truly understand what the other person is saying or trying to say. There is a lot that the mind misses out, such as the tone in which they are saying things, the body language, and so on. Practicing active listening requires you to restrain yourself from these tendencies and be truly and fully present in every conversation.
3. Don’t launch into selling your product/demo right off the bat
It can be tempting to launch right into presentation and demo mode after a perfunctory introduction with a prospect. Doing so too soon can actually hurt your chances of winning their business. This might be counterintuitive initially, but it will become clear when you realize that a first meeting with a prospect rarely turns into a signed deal.
You do this by showing genuine curiosity and asking probing questions while, at the same time, balancing that by offering insights from other industry peers or sharing your unique and specialized knowledge about the problem.
This is also your opportunity to figure out whether you are speaking to a champion, the economic buyer, an influencer, or just a friendly person. Oftentimes, friendly people who offer you information but otherwise lack authority or influence are not a good use of your time (Are you a cybersecurity founder? If so, read more about the types of buyers from my colleague, Ken Elefant).
4. Closely track your learnings from sales calls
Automated note-takers have become ubiquitous these days. Unfortunately, taking notes (automated or manual) alone doesn’t lead to learning.
In order to truly extract the prospect’s intent and other key signals, you need to spend some time doing post mortems on meetings-including those that seemed to have gone well. Doing so systematically, will help you lay the foundation for what will hopefully become a repeatable sales process in the future.
For every prospect, create a document that captures what you learned about their pain points, their tech stack, their key vendors, their influencers, champions, economic buyers, business priorities, their as-is process and their future aspirations (if any), sense of pain, urgency, perception of the market/competitors, who you met with, along with timelines.
You might want to take an hour or two at the end of the work week to track all your learnings for the week if you want to batch this effort. And yes, this is asking a lot of a founder to do.
The nuance is often hidden in plain sight and the process of reflecting on your conversations is a great way to unravel it!
5. Don’t do POCs just because a customer asks you to
You just had a GREAT first call with a prospect. You did the pitch, they instantly got it, and said they would love to do a POC. Sounds amazing, right? Not so fast! Getting quickly to a POC can feel like a win in itself and as a sign of progress. Poorly qualified POCs lead to a total waste of your finite time and resources and will rarely be a repeatable process.
Technical champions might sometimes show interest in solutions for the purpose of augmenting their resumes and have no clear business need. POCs pursued by such folks often result in no deals or deals that are incongruent to the amount of time and resources that gets consumed in their pursuit.
Remember that busy activity alone will not guarantee results. Too many poorly qualified POCs are much worse for your business than a smaller number of highly qualified ones.
6. Manage your pipeline—it’s your lifeline
Create at least three distinct stages to track every deal through your pipeline.
Remember that both quantity and quality of deals are important in order to have a healthy pipeline. Let’s say you want to go from $0 to $500K in ARR over the next 3 quarters, with the goal of closing $50K, $150K, $300K in each of the coming quarters, and have a typical large enterprise sales cycle of 9 months. Assuming a 50% conversion rate per stage, you need to have $100K worth of late-stage deals in your pipeline to close $50K this quarter, $300K mid-funnel deals that can deliver 150K next quarter, and do enough early-stage discovery calls in order to bring have a $600K pipeline for the third quarter.
Finally, just like how you would weed out unhealthy plants and weeds to maintain a healthy garden, you should do the same with your pipeline on a weekly basis. At least every Friday, be ruthless about moving customers out of your pipeline when you find they lack urgency, lack budgets, or have engagement processes that are too complex and prolonged.
7. Multi-thread your approach for complex sales
Oftentimes, late-stage deals are in jeopardy because the champion leaves or has suddenly become unresponsive. If you cannot continue the relationship with an alternate key stakeholder immediately, your deal is practically dead.
Now, most large enterprise sales deals involve multiple stakeholders even if there is only a single champion and/or economic buyer. While you don’t want to overinvest and over connect with people at every large enterprise account, it helps to have some touchpoints with a few key stakeholders besides just the champion and economic buyer. This can be as simple as sending them newsletters, product announcements, whitepapers, invitations to events, and the like. You don’t want to be a complete stranger to a new potential champion or buyer if your original contacts leave.
8. Really sharpen your ICP
Your ideal customer profile (ICP) is not just a person with a particular title in a specific industry. For example, CISOs and CIOs in regulated industries such as Financial Services are still too broad–it is not actionable enough to finetune your early-stage founder-led sales.
Founder-led sales is essential not to take multiple years to achieve. If, as a seed-stage startup, you set your sights on a 6-figure deal in Bank of America (BofA), you will most likely brace yourself for a sales cycle that might take 18+ months if you are lucky. This is neither BofA’s nor your fault. There is just a huge impedance mismatch between a fledgling startup and a large risk-averse enterprise that takes credibility and time to overcome.
Think more deeply about what would cause a financial services company to buy and buy sooner rather than later. Could it be a potential license renewal of a particularly expensive or non-innovative incumbent? What about other pre-conditions that might lend themselves to be more fertile ground? For example, do they have a critical mass of security engineers that they want the problem solved? But not too many that they will pursue DIY. What about other aspects of their tech stack that prepare them for you sooner than later (e.g., they are on AWS, use Databricks, have a SIEM etc.)?
9. Don’t go to events without creating a list of highly relevant attendees that you are trying to meet
Even in the early days, attending conferences or events where your ICP is in attendance can be tempting. After all, you want to be seen and known in your community of users and buyers. There isn’t anything inherently wrong with this unless you are limiting yourself by hoping that the “right” people will find you. Hope alone has never been a great strategy.
Instead, take the time to comb through the speakers and attendees listed. See which logos and kinds of people you want to talk to–this is your VIP list. None of the people you list might even run into you or stop at your booth. You need to put in the effort and reach out and connect. Make a deliberate plan. If you are lucky to have multiple people attending events, at least one of you should be actively pursuing your VIP list of prospects– attend their talks and see if you can get facetime right after their talks.
10. Get comfortable with cold-calling
When I say cold-calling, I am referring to any kind of outreach one makes to a stranger–via email, in-person, or over the phone.
Now, there is a firmly held myth out there that cold-calling is something that only hired salespeople do. Unfortunately, this is a seriously self-limiting belief. Cold-calling can be a powerful skill to cultivate and use. A related myth is that only extroverts can cold-call. Again, nothing can be further from the truth. According to Leslie Venetz, the consummate cold-calling expert, there is a complete science to cold-calling. And it can summarized in a few essential principles:
- Prepare and know your audience and what they care about.
- Keep your message brief, less than a hundred words, with a single call to action.
- Finally, earn the right to their time, attention, and consideration. Think about what you have done to expect this from them.
Finally, cold-calling should be treated like any learned skill. No one is born with all the skills they need to thrive in this world, after all—especially founders!
See you at the top, and please reach out if you’d like to connect!
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