Founder-Led Enterprise Sales Notes: Observations Across 40+ Early-Stage Companies
This is a living, breathing compilation of founder-led sales expertise I have organized after working with more than 40 early-stage VC companies (Seed to C) over the past 5+ years. I have further enriched it with transcribed conversations I have had with CEOs who have generated revenues of up to 100MM per year. The patterns of what works and what doesn't are quite interesting. Below, I share these observations. However, they are not to be taken as truth since all heuristics have limitations due to context-specific nuances.
Founders have used these principles to achieve numerous forms of business impact such as:
Profitability.
0 to 5 MM ARR in less than 12 months.
Shift from a tech-enabled service company to a SaaS company.
Raising fresh rounds of VC funding.
Prove out a recurring revenue stream and move away from transactional.
Streamlined their GTM/Product choreography.
Published: August 25, 2025
(Note: whenever I can, I will update this document with new findings or refinements.)
Takeaways
Subject Matter Expertise
Founders must understand their customer's role and challenges better than the customers themselves (e.g. unique point of view, unique insight etc.) so that during initial conversations, the customer feels like they need the founder as a partner to solve those problems going forward.
Before the product is fully-baked, especially at the enterprise (or more upmarket GTM motions)– the founder is a big part of the product. Often, you are scaling and evolving their expertise and passion through a combination of: products, people (employees), and systems.
Founders often also have the advantage of providing the psychological safety needed for customers to take more risk to solve a painful problem. Especially if they haven't ever had success in solving that problem effectively and sustainably. That founder is often the one to say “despite your past shortfalls… the future can be bright!” Founders who are effective at changing their customers' beliefs will be surprised at how much impact they can have, especially if the buyer is a key leader at their company.
Sales Talent
Hiring sales talent at this stage doesn't mean the founder can step back. Even with a salesperson on board, the founder will still be doing a majority of the sales work. The salesperson's role is more about supporting the founder (outreach, collateral, deal management etc.) rather than taking over the sales process entirely so that the team as a whole can handle more deals.
Founders should not expect to find a salesperson who can independently handle early-stage sales without their involvement. This expectation is unrealistic because the startup is an unknown entity with an unproven value proposition– it is rare (almost non-existent) to find a 0 to 1 sales person because that person is likely to be working on their own startup (aka they are a founder!).
Founder Management
There is a significant aspect of managing the founder in early-stage sales. Salespeople need to work closely with the founder to ensure they are effectively involved in the sales process and leveraging their expertise to build trust with potential customers. Early sales people should be expected to be proactive in activating and creating leverage for the founder.
Salespeople will not be able to inspire like the founder. Founders who expect salespeople to be able to do advanced enrollment and reframing in C-suite level conversations are kidding themselves– these founders will be chronically frustrated at the lack of speed and progress.
Product-Market Fit
Be open to pivoting to different customers, potential adjacent markets, based on customer feedback and initial sales experiences.
Pmf is just one important component since pmf doesn’t guarantee high volume and low-cost customer acquisition at scale– the buyer is often different to the user. Therefore, it helps to understand the 4-fits needed to build a VC-scaleable company.
Direct Customer Engagement
Founders must engage directly with customers, especially in the early stages. Relying on third parties for direct sales before achieving product-market fit is generally ineffective. While this is a tough temptation to avoid in practice, more often than not, successful founders stay at the helm of sales efforts longer than they would like.
These early customers will be a strong referral source and/or case study for future sales efforts.
Sourcing
Founders and their investor networks are some of the best people to tap for warm introductions to potential customers. While cold outbound campaigns are great, they are often costly and time-consuming.
A founder who prospects via warm requests for introduction (or direct CEO to CEO outreach) will have greater conversions for a discovery call, and a higher likelihood of success throughout the sales motion.
At some stage, it helps to have a sales hire (or a hire like a CoS or Biz Ops) to help scale outreach and sourcing.
Sourcing customers and introductions through networks is a social activity– nothing activates the social brain better than being in company with one another. Consider a group pipeline party (in person or on Zoom) – names and faces magically appear out of people’s memory banks in real-time.
Don’t self-impose limits on who can make helpful introductions– people are so much more than their professional titles and roles. You will be surprised.
There is never too much top of the funnel– most of the time deals will take longer to close. Your hedge is plenty on top of the funnel. You want a more statistically significant data set.
Industry events and conferences can be extremely valuable especially if the founder is a speaker or guest panelist. In absence of this, highly curated dinners work too.
Whenever you can– go top-down. It is strange for an IC level person at the enterprise to speak with the CEO.
Scheduling meetings tip– If someone is making a connection to a C-suite or executive for you based on your Request for Intro (RFI)– you are asking for their time. Therefore, the etiquette is they will either offer options (or copy their EA to coordinate)– you choose the time slot that you can make work. If you are asking for someone’s time, do not provide an auto-scheduling link (e.g. calendly) in your email– this can come across as an abrasive touch.
Managing Scale and Volume
Founders leading their sales motion for whatever reason – fine-tuning product and channel strategy, or, pivoting their company out of necessity – will find that their conversions to first-meetings are incredibly high compared to your standard SDR.
E.g. Outreach to 100 relevant individuals could yield 20-30% (or more) conversions to first meetings.
After 200, assuming their value proposition makes sense and is high enough of a strategic priority, founders will find that they can't feasibly move and manage all the promising deals going to procurement. This can happen as quickly as a month!
At this stage, you will have earned the right to tackle the next problem which is scaling their efforts while sustaining them:
Moving all the deals to a close.
Identifying which deals to prioritize.
Continued sourcing and top-of-funnel generation.
You might consider (within constraints of funding) investing in a fractional sales leader or fractional CRO to help– especially someone who is scrappy and experienced working in the early/early-growth stage of startups. Aside from being experienced, you can tap their networks for key new hires, and in some instances, they can even open doors to ICP’s for you.
Have some sales operational support (or from a hire like a CoS or Biz Ops) to help:
Scale your continued outreach. E.g. Sourcing and customizing some thoughtful customized messaging for outreach.
Project manage deals. E.g. prepare presentations, organize materials for different procurement processes, managing expectations and deadlines.
Document and can transfer context and process to those helping you:
Template messaging
Template workflows
A clear understanding of stakeholders, what matters to them, and why.
Taking a Risk-Reward Approach to Early-Stage Sales Efforts
Treat GTM strategy as a science experiment, using a process of elimination to identify what works. This involves testing hypotheses, analyzing results, and refining strategies based on feedback. This is true for all other aspects of business too. You want to prioritize experiments based on:
Hypothesized business impact.
Resource constraint.
Probability of success, and
Estimated time to impact.
Specificity in Solutions
Focus on solving highly specific problems rather than broad, abstract issues. Identify and address specific, measurable problems that customers face. Specific solutions build trust and resonate more with customers. You are more likely to have an early successful sale – this becomes a platform for expansion.
Avoid leading with broad or abstract concepts (albeit important) like "AI", “Workforce Transformation” etc. without tying them to concrete benefits. Rather, you might want to focus on specific things like “automate management of 1099’s for tens of thousands of influencers you use.” or “Identify and recover 300K+ rejected claims in minutes not months.” or “Optimize and automate efficient pricing across your 200 channels at a click of a button to increase sales by 30% over a 2 week period.”
Sales is Both About Revenue Growth and Research
Sales is a necessity if you want to achieve your next fundraising milestone– but it is also important to use it for research to answer the hard questions.
Are we solving the right thing?
Does solving this lead to a venture-scalable business?
What big questions do we want answered?
What assumptions do we want to prove/disprove?
Allocate up to 18 months for the initial market research phase. Use this time to understand your market, validate your product, and refine your approach before scaling sales efforts. The holy grail is being paid to learn.
Sales & CX is About Helping Customers Avoid Self-Sabotage
Early-stage founders are often confronted with customers who want and need their transformative solution, however, are addicted to maintaining the status quo.
Using physical servers.
Needing numerous integrations with old tech.
Irrational resistance to the solution such as “Why would I pay for a tech solution to put me out of a job?”
Resource constraints to invest in your solution due to political tensions within the organization.
Blaming vendors for failures versus taking responsibility for their inputs in the partnership.
Often, having a solution that works is only part of the challenge. Getting the customer to embrace the solution effectively is the bigger challenge. People will defend their limitations. The same phenomenon occurs amongst organized groups of humans (e.g. companies). The status quo is the status quo because it is sticky. Founders leading their sales motions are confronted with reframing and enrolling customers to a new paradigm, and providing the psychological safety and reinforcement necessary to create a new status quo.
Relationships Relationships… Relationships
Sales and business is a human enterprise. As much as we would like the product to do all the talking– the customer (buyers and users of your product) for now is a human being (or a collection of human beings).
Like all worthwhile and enduring relationships, you must normalize that there will be difficulties you confront together, however, confronting them together will lead to better short-term and long-term outcomes than not. To do this, you must:
Ask the difficult questions up front in the sales process:
What has worked in the past?
What hasn’t worked well, and why?
What are the biggest hurdles or blocks you anticipate I will need to work through assuming we do business together?
Who else do I need to speak to settle their concerns or apprehensions?
Managing the relationship through trust, transparency, and collaboration. Healthy relationships involve confronting challenges (often unforeseen ones).
Sometimes the customer lets you down in helping them. Sometimes you and your solution lets the customer down.
Is there a system for truthful, fast feedback, and a culture of solving things together? That’s how relationships are strengthened.
Do they feel safe to tell you difficult truths? Do you feel safe telling them difficult truths?
Enterprise Deals are About Landing and Expanding
The initial landing of a deal is important, but true value comes from expanding the contract year-over-year. If there isn't regular expansion, you want to ask the question “Why?” and “How can we expand?”
Assuming you solve the initial problem you were engaged to solve, you are now in a position of trust and familiarity– people at the company know you. So, unless a better solution comes along (with a team that is easy or easier to work with than yours) – you are in a strong position to upsell. Your advantage in landing is you have information about the enterprise (how they work, their strengths, problems, weaknesses) that is not publicly available information to your competitors.
Enterprise contract values typically start with a small pilot followed by a larger pilot and then a proper rollout (e.g.6-7 figure contracts).
Sales + CX + Product Collaboration
Sales + CX + Product representatives must work together to create more value from and for existing customers by leveraging the trust already established. These three functions are always looking at ways to:
Expand through new offerings and packages.
Retain the customers so that churn risk is as close to 0% as possible.
Improve product dependency/utilization.
The challenge is that the buyer and user are often not the same person. A product that users love doesn’t always mean a product that buyers keep paying for year on year. Therefore, you have to look at the enterprise as a series of important stakeholders with unique needs and priorities– identify what they are and how you can use them to your advantage.
Large Logos Are Significant
A significant portion of revenue for large tech companies comes from their major enterprise clients. There is natural revenue concentration. No single point of failure. However, this underscores the importance of expanding these relationships for long-term revenue growth.
Embrace Service Revenue Thoughtfully
Many founders shy away from service revenue due to VC opinions (e.g. is this really a tech company? I don’t like the margins etc.). However, that service revenue can be a strategic entry point:
Once a company is "in," they can leverage the insider information gained through service engagements to better tailor their tech solutions and expand their value offering
Enterprises have big budgets for services consultants, and, typically less onerous requirements during procurement and contracting. This can accelerate your sales cycle. There are different budgets within enterprises, such as talent, services, and tools and technology budgets. Instead of competing for the same tech budget, companies can tap into the larger services budget as a way to get their foot in the door. By securing service contracts, companies can later parallel-track these into tech sales as the relationship and trust deepens.
Status is a Human Driver
Whenever you are working with a complex group of stakeholders, remember to reverse engineer their incentives and behaviors so you understand how to motivate them to take actions in your favor.
Whether you admit it or not, every human being is driven at some level by these three questions when it comes to decision-making:
Does this make me look good or does this make me look bad?
How can I look good?
How can I avoid looking bad?
To be competent at status games, you must understand what elevates or diminishes your (and others’) status as it applies to a specific ecosystem.