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The (Early Stage) Enterprise Sales Bible

The (Early Stage) Enterprise Sales Bible

A running list of insights for sales-led growth for early-stage startups

January 02, 2025

Last update: 01/02/2025. This is a living, breathing blog post. I’ll periodically add learnings that I’ve accumulated.

Rameez Tase is the Co-founder & President of Antenna, a leading provider of advanced data analytics for subscription businesses. Rameez has spent much of the past decade in founder-led enterprise sales, selling large contracts (well into the six figures of annual value) to large companies (including many fortune 100 brands).

Sales-led Growth for Startups

B2B founders are drowning in a sea of Product-Led Growth (‘PLG’) advice following the past decade of PLG dominance. PLG can be amazing for the right product / market / customer combo. But I believe the art of enterprise sales is primed for a renaissance. Many enterprise startups who have scaled on PLG recognize the key to unlock their next wave of growth is through Sales-Led Growth (‘SLG’). But after a decade of PLG, do startups even remember how to do SLG? At Antenna, we’ve focused on SLG from day 1; here’s an aggregation of all the lessons I’ve learned over the past 6 years.

Enterprise Means Enterprise

I’m talking about 6-7 figure deals with Fortune 500 brands. I am expressly not talking about anything below this. Mid-market deal sizes cannot support enterprise GTM and client service models and, if that’s you, it’s better to acknowledge that upfront.

Features of this Model

Enterprise sales is a high ACV, high touch servicing model. That does not mean it is a professional services model, though professional services is often an important component. This high touch requires robust staffing, and a ton of operational efficiency (along with those high ACVs) to cover costs. Sales cycles can often eclipse a year, as client buying cycles are often done on an annual basis. Enterprise sales is high-friction on the way up, and it’s also high-friction on the way down. Once you are adopted, the switching costs are extremely high. While the higher friction of SLG makes it harder to run a venture-style, asymmetric growth playbook, the higher switching costs make it exceptional for building a sustainable business. In any event, even the most successful PLG startups reach a point where they must go upmarket and learn this SLG motion — and often, it’s an enigma to them.

The Early Stage Enterprise Sales Bible

Getting it Right on Day One Matters a Lot

Product-oriented founders are often skeptical of the importance of enterprise sales. Let me highlight the importance of getting it right with a hypothetical example.

Let’s assume that your product has product-market fit with SMBs. Now, you are taking it to your ideal enterprise customer but haven’t built out a proper SLG function. Case study: Nike.

Assume Nike has 10 departments, each headed by a GM / brand manager. Across those brands, Nike pays $10M for the incumbent service; $1M of which is funded just by the Jordan brand. Here’s what could happen if you get it wrong:

Scenario A (worst case): You get a pilot with the Jordan brand but don’t have enterprise customer success built out. Jordan chooses not to convert from the pilot — and they recommend the other 9 departments don’t consider your services either. That’s $10M of potential recurring revenue opportunity cost.
Scenario B (best case): You do impress Jordan but have started them on SMB pricing because you don’t have an enterprise rate card yet and, besides, “it’s just a pilot.” Now you’ve anchored to a price point a fraction of Jordan’s $1M willingness to pay — and the procurement team who represents the other 9 departments knows that. You haven’t lost all $10M of potential revenue but, even in success, you’ve lost most of it.

OK, so it’s agreed then: learning how to do this well before you waste your shots on goal is very important.

How Enterprise Clients Buy

Enterprises buy in the exact opposite way of startups. Whereas startups want to pay usage-based pricing and grow into a solution, enterprises’ first buy is often substantial, and at the point they buy, they are fully committed for the long-term.

Fixed vs. Variable costs: Whereas startups love to buy software on a variable cost basis (e.g. usage-based, % of sales) since this allows them to start small, enterprises hate it because, at scaled usage, variable costs add up, and disincentivize usage. For that reason, enterprises would much prefer to pay a fixed cost for AYCE access. But, because this AYCE price is likely very high, they will want to go through a long evaluation cycle before they commit. 99% of the magic of enterprise sales happens during this gap between interest and commitment: how do you convince them?
Annual budgeting: Most large companies budget on an annual basis and asking for additional budget outside of that cycle is difficult. Within the budgeting cycle, if you have worked with your champion to build a case they can bring to the budgeting process, it is very normal for new spend to be approved. Outside of cycle, the budget needs to come from: (a) another vendor, (b) a small, experimental budget, or (c) a CxO overruling the budget because of urgent need. Know this in advance and use it to your advantage (e.g. tap a small, experimental budget in the quest of the end of year budget conversion). Build your pilot lengths in anticipation for this.
Client champions: One of the core competencies for executives at large companies (VP and above) is their ability to successfully identify, buy, and onboard vendors to solve business problems. These executives are often very sophisticated about how the process works and, if they believe you can help them on their performance review, actually want to work to help you. Step #1: Find a product that solves one of these pains. Step #2: Find the executive who will benefit from solving it (or in reverse order). Step #3: Profit.
Buyer ≠ user: When you find this champion, it’s likely they aren’t your user. They do not want to see a product demo (the most natural follow-up in mid-market sales). They want a document acknowledging you understand their pain and a summary of how you intend to solve it. This is necessary-but-not-sufficient. You must, now, go find the user as well (or in reverse order).
1. Multithreading: The process of reaching out to multiple levels of seniority to understand the problem from user, buyer, and executive champion points of view.
Onboarding: At the point of purchase, enterprises have often onboarded dozens (if not hundreds or thousands) of users onto a solution. Thus, a purchase decision means much more than “we’ll try it.” Structure your pilot phase to clear this bar.

Developing New Products for Enterprise

Given how clients buy, SLG product development is very different than PLG product development. in SLG, products are often concepted with a small group of customers, in private beta, before they are released publicly. This minimizes chances of failure: when your market is limited, even your MVP has to clear a pretty high bar.

Sales = Product Discovery: In PLG, product discovery consists of putting an MVP into the wild and iterating based on how prospective customers react. In SLG, product discovery consists of months of conversations with clients where you co-create a product together with the end goal of an enterprise partnership. This means that:
1. MVPs are often shipped behind closed doors, not on for all to see. Your sample size for product discovery is much smaller. Connecting the dots between product vision, sales model, and product execution on a limited n is integral.
2. The cost of burning a lead is much higher. If your entire TAM is the Fortune 100, and you have a bad new product discovery process with 5, you have lost 5% of your TAM just like that. The founder must be involved to ensure this doesn’t happen.
3. One client’s MVP will not look exactly like another. Navigating the how custom is too custom question will be a recurring topic on the executive team agenda. The only wrong answer for the enterprise is we will offer no customization.
Founder = Head of Sales = Head of Product: Because of this connection between sales and product development, your Head of Sales is actually your Head of Product. There is no one who can possibly more intricately understand what to build than the person who spends their time convincing customers. And, because it is an unrealistic expectation to ask a Head of Sales to also be your Head of Product, the Founder must be both.
Client development partners: Your products will be concepted privately, in collaboration with customers. This extends the timeline of development, results in some custom features, and limits the immediate buyer universe. Your customers know this. They are accustomed to paying for the privilege to co-create a new product, that solves a pain point, in partnership with a trusted vendor. Have two launches: first, your private beta with a few paid development partners; and then, your first launch that is more widely available.
Three-headed products: When designing the user interface, keep in mind that you effectively need three interfaces: one for each the user, buyer, and executive champion. The “interface” for an executive champion can be as simple as a slide deck or email. But, without an intentional touch point for each layer of the stack, you will lose.
Professional services bundled in: Yes, this costs money. Yes, you should do it anyways. Increase your ACV to make room for it. Clients would rather pay to get platinum service than pay almost as much without it. This is a huge departure from PLG thinking. A PLG expert would say if you need professional services, you aren’t building a good enough product. While this may be true, it is often not the case for many successful SLG companies. An SLG rebuttal may go something like this: what you see as cost, we see as an opportunity to get in front of executive stakeholders in a very high touch way. And, at the same time, don’t get sucked into becoming a services company. The software is the must-have, the services enable success.

Sales

Sales efforts must mirror the buying cycle. Because clients prefer to buy with larger, fixed cost contracts; and must align many internal stakeholders (procurement, other users, etc); sales cycles will be long. However, most SLG companies need this long period of time in order to clear the high bar at the end of the rainbow. At the point at which the client is ready to make a buy, they are often ready to roll it out to many users. Rather than sitting back, use the time in between first contract and the big buy wisely.

Founder-led: Existing B2B wisdom posits that the founder should be involved the first $1M in ARR. For enterprise sales, the founder should lead the first $1M and, in most cases, much more.
1. Why? Because enterprise deals are pretty bespoke, and sales cycles can be 6-12+ months, establishing proper pattern matching is tough. The consequence is that it’s difficult to onboard sales reps to a playbook until well beyond $1M in ARR, which means the founder must stay intricately involved for what seems like forever.
2. Don’t expect this to stop. Even when you get to $10M in ARR, don’t expect to be out of the weeds. If you build a successful first product your enterprise clients love, guess what, they’re going to push you to build a second. Enterprises love consolidating into trusted vendor partners. When this happens, you’ll be doing founder-led, sales-led discovery all over again for a new client pain.
  1. Related: there is a close correlation between enterprise-led, focus on specific vertical(s), and therefore, needing to go multi-product early
3. This means that the profile of your first sales reps should be more like chiefs of staff. Hire SDR-AE-Sales Ops combos who are young & hungry enough to support you as the primary AE.
Repeat the best practices: Find a champion. Multithread. Lead with services. Co-create new products.
Consider hiring domain specialists: The bigger the contract, the more consultative the sale, the higher the customer expects a domain-fluent sales rep, the less success horizontal sellers will do. We’ve had a terrible time at Antenna (a data & analytics company) hiring sellers whose previous experience was vanilla SaaS or whose ICP was SMB.
Sales CRM: Many companies organize their CRM by company / logo. Doing this in an enterprise context will almost surely lead you to underestimate your TAM. Within a single company, there will likely be multiple departments who can buy your product. This might be various brands within a retailer, like in the Nike example.

Pricing

There is a massive gap between PLG and SLG companies on pricing and, the most shocking part is, no matter how early stage, SLG companies must have a mature approach to pricing. Unlike PLG, where pricing is often variable based on usage or seats, and customers aplenty so a few early pricing integrity lapses can be overlooked, lax early policies will haunt you for years to come.

It’s almost impossible to price too high: ‘nuff said. And, if you’re in the 1% who do, the market will negotiate you down, and buy your solution at the market clearing price. If you are not routinely losing deals over price, your price is much too low.
Pricing is rarely the lever: It is highly unlikely that reducing price is the first, second, or third reason a disinterested prospect isn’t buying. Generally, enterprises are somewhat price insensitive for must-have solutions. They are also very open to increased value to justify price.
Price discrimination: Standard methods include usage-based pricing and seats-based pricing. However, when your contracts are more AYCE-style, you must find other ways. That may be done by duration, department / business unit, or putting certain features behind a paywall. Save the true enterprise-wide AYCE offering for a price so high that no one would be willing to pay it without years of experience working with you.
Procurement departments: All large companies have procurement departments whose primary function is to reduce cost and increase value for the business. No matter how early stage your company is, at a certain contract value, you will have to get past procurement. This means you need to invest in dealing with procurement from day 1, or it will haunt you for the remainder of your relationship with that customer.
1. Communicate pricing expectations: Ensure your market rates / terminal pricing are clear if you are giving discounts. Ensure access and other key requirements are clear. Do this in writing in the contract. These create anchors for years to come.
2. Price and value are linked: If you are getting negotiated down on price, the easiest response is to bring value down in response.
3. Define success: The more you can define about what you will deliver, and how to measure whether it is successful, the better. Procurement is not a subject-matter expert in what you are selling but they are often responsible for measuring success. And, if they write the rules, the bar will be harder to clear, and you will be penalized for it in renewal.
Legal operates similarly: You will also have to deal with a legal department past a certain size. Signing Master Agreements with companies is amazing; it makes working with them in the future much easier. However, the requirements in these agreements can verge on ruinous. Or the insurance policy you’re required to take out may be enormous. Be patient and don’t ruin your entire company just for one deal. Often, the net of this is that your finance & operations muscle needs to be overbuilt early on.
Have real conversations with customers: Be upfront and transactional in a good way (much easier if you’re the founder). You started this business to solve their pain. Based on their feedback, you made certain decisions. If you cannot make a certain amount of money, there will be no business. If they value your service, that is a problem that must be solved together.

Client Service

Investing in Client Service is highly important to justify large contract values, ensure retention / expansion, and invite the opportunity to build new products within the organization. In PLG, client service can be overlooked as a cost center, but in SLG, client service can rival sales as a revenue generator given how much future revenue is available from current clients at an early stage SLG company.

Customer Success: Deliver a successful product to the day-to-day users. Ensure any release notes are sent. Review new features. Capture inbound product feedback. Note: there is a wide gulf between what CS looks like at a PLG company (sometimes closer to a call center) and SLG company (highly functioning, six figure employee). These CS reps can often support a couple million dollars in annual contract value.
Feature Improvements: Feature improvements, which CS reps will funnel to the product team, should be prioritized based on their likelihood to create NRR. Because your customers will be extremely direct with you, this prioritization process does not have to involve a lot of guesswork — you can ask your customers directly!
Account Management: Separate from CS, is AM. At large enterprise companies, these are two separate roles. The primary differentiator is that the AM focuses outside of day-to-day users. They build relationships, and mine the org for additional use cases on the existing product suite, as well as pain points that the company may build new products to solve. These are highly paid senior sales executives who often bring in as much business as top AEs. They can be responsible for millions in incremental revenue each year.
Editorial / Insights: For many products, having some sort of insights function sitting on top of the data is essential to drive value. For example:
1. For an analytics tool, having blind benchmarks to help your customers answer the question “what does good look like.” Profitwell has done a great job of this.
2. For many SaaS applications that collect data indirectly from customers, there are many stories to be told. Carta does a great job at this.
3. For ICP-specific tools, content that helps your customer do their job is gold. Measured.com, which is focused on marketing analytics, does a great job here.
4. For complex software tools with a steep GTM ramp, spelling out all the ways you can use the product is necessary. Looker.com is well-versed in suggesting use cases.