Enterprise Sales: What does it mean for startups

By Supratim Biswas & Anil Kumar

Hunters and Farmers

In sales, there are the farmers and the hunters. Hunters are the hungry face of sales—they hunt new logos, kickstart relationships, and manage them until they’re called “whales.” Farmers, on the other hand, are more focused on account management, expanding existing accounts, and building revenue over time.

Enterprise sales combine both roles, but it’s a unique beast that requires a consultative approach, aiming for long-term customer value. The enterprise sales model isn’t just about hustling or closing deals; it’s about unlocking high-value opportunities and creating transformative partnerships that ideally result in a hockey-stick growth trajectory. The most successful enterprise salespeople are not “show me the money-themed hustlers”, instead they are well-rounded personalities, who act as friends, philosophers, and guides to their stakeholders.

The Allure of Enterprise Sales for Startups

The world of enterprise sales, often called complex sales, is a desired destination for many startups because of its potential to:

• Create your brand: Built on a track record of integrity and discipline
• Sell to big brands: Working with recognized companies builds credibility 101, know your ICP first
• Expand opportunities: Enterprise accounts offer a broader playing field for your product
• Deliver massive impact: The outcomes are meaningful and high-value.
• Generate significant revenue: Multi-year, multi-million-dollar contracts can provide a stable foundation for growth.

However, enterprise sales are notoriously challenging to navigate. It’s not about selling a product; it’s about delivering outcomes. A sales rep often starts a process not knowing exactly what they’re selling, because enterprise sales involves working closely with the customer to identify their needs and tailor a solution that combines products, services, and processes.

Enterprise Sales and Startups

For startups, enterprise sales often fall into one of three categories:

1. Not Ready for Enterprise: These startups do not currently sell to large enterprises.
2. Aspiring to Be Enterprise-Grade: These startups sell specialized products to small teams within large companies, targeting specific user groups who can pay without executive approval. Deals are small (under $25K), but early traction creates opportunities to expand into larger cross-functional teams. This is the classic land-and-expand strategy, where initial proof of value leads to larger contracts over time (e.g., Slack, Figma, Atlassian, Stripe).
3. Enterprise-First: These startups sell complex solutions directly to large enterprises. The sales process is consultative, requiring co-creation with stakeholders, alignment on ROI, and navigating long sales cycles that often span months. Deal sizes are typically multi-million-dollar, with implementations involving deep integration into the customer’s ecosystem (e.g., Salesforce, Snowflake, Databricks).

Is Enterprise Sales Different?

Enterprise sales are vastly different from other sales models due to their complexity. Legacy systems, entrenched processes, and long-term contracts create an environment where CXOs and decision-makers are risk-averse and resistant to change. Good strong CXO relationships are key to long-term value being delivered

For SMB and mid-market sales, the focus is narrower, often solving a specific challenge with fewer stakeholders involved and shorter sales cycles. For instance:

• Selling communication APIs to a local e-commerce brand may involve a quick demo and a fast order turnaround.
• Selling the same product to a global e-commerce giant like Amazon requires addressing multi-country operations, load scenarios, integration with existing systems, and obtaining approvals from multiple stakeholders, making the sales cycle significantly longer.

When Is Enterprise Sales Right for Your Startup?

1. Embedded Client DNA: Success requires understanding the client’s ecosystem, challenges, and goals. A salesperson must master the mix of business acumen, technical knowledge, and relationship-building to navigate complex environments and be the consultant not afraid to say no and renavigate to play the long game if needed.
2. Product-Market Fit: If your product solves a high-value, complex problem and is priced for large-scale adoption, enterprise sales could be a fit. This is especially true for companies in data infrastructure, systems of record, or cutting-edge technologies (e.g., Databricks, Salesforce, OpenAI).
3. Hunting Elephants: With large deal sizes and multi-year contracts, enterprise sales can provide stable revenue. A few well-executed deals can create a strong foundation for growth and future expansions.
4. Relationships That Drive Innovation: Deep relationships with enterprise clients can lead to bespoke solutions and product evolution, making your offering more valuable over time.
5. Credibility Through Big Logos: Landing world-class customers like Apple, Walmart, or JP Morgan gives your company a halo of credibility, making it easier to attract additional enterprise clients.

Key Challenges for Enterprise Sales

The main challenge is to build an enterprise sales model that is scalable. The key questions before getting started are :

• Identify your target market and the logos you need to crack
• Define a clear GTM strategy focused on a consultative selling approach that understands challenges and makes recommendations that are based on customer business priorities?
• Identify the personal success factors of your stakeholders and ensure they are discovered, keeping in mind the possible detractors or fans of your competition
• Develop a sales process that aligns with customer outcomes and integrates your product into their ecosystem
• Become the consultant, and not the short-term hustler trying to crack a deal, think, breathe, and deliver long-term customer customer value?

You know you have enterprise-grade PMF? if your customers adopt the product and realize value from the product which will eventually result in retention and expansion.? We like a composite health score for enterprise deals tracked over time ( See below)

Building the Right Enterprise Sales Team

• Hire experienced Sales “Consultants”: Enterprise sales requires elephant hunters-seasoned reps who excel at navigating complex environments and building trust with senior stakeholders.
• The elephant hunters are mature and solution-oriented (as opposed to sales-driven only), and build trust with the client chain of stakeholders
• They must work well with the internal product teams and operations enablers to ensure they work together to ensure the client gets the value they hoped for and ensure it is delivered, time and again
• Balance hunters and farmers: A strong mix of new logo acquisition (hunters) and account management (farmers) is critical for success.

Developing the Right Sales Tools

• The product training: Focussed on identifying the problem set and challenges, and then building the bill of materials to retrofit the organization's needs, which may need collaboration with other product vendors that form a part of the solution needed to deliver on the larger promise-Orchestearte the delivery
• CRM Systems: Use enterprise-grade tools to track long sales cycles and manage multi-stakeholder deals effectively, and internal tools for collaboration that along with the solutions needed to address customer needs and long-term
• Enablement Resources: Provide sales teams with playbooks, ROI calculators, and case studies to support consultative conversations.
• Incentives that motivate rather than devalue their value by economizing and shortchanging their efforts-a Pat on the back and impromptu rewards work nicely

Metrics and KPIs

We? must track a set of interconnected metrics that provide a clear picture of pipeline health and pipeline velocity. These KPIs include?

• Opportunities Created: The number of deals entering your pipeline.
• Sales Cycle Length: The time it takes to move deals from prospecting to close.
• Win Rates: The percentage of deals your team successfully wins.
• Average Sales Price (ASP): The value of a typical deal.
• Customer Acquisition Cost (CAC): The fully loaded cost of acquiring a customer, including marketing, sales salaries, and tools.

You can calculate sales velocity as

These metrics are not just numbers to track, they are levers to pull, analyze, and optimize to drive scalable growth. For example, increasing your win rate or reducing your sales cycle length can dramatically improve sales productivity and accelerate revenue growth.

Scalerz Take:

• Enterprise sales may not be the right market entry strategy for 95% of startups. Most startups should evolve to enterprise sales over time. Remember both your product and sale process must be enterprise-grade to win.
• Enterprise sales is complex, it takes time despite the best plans, so be deliberate and plan to stay for the long haul to get it right. Be very selective about your initial few customers, the idea with the first couple of deals is to prove enterprise value and not scrape the last dollar. You will learn together but only if needs match expectations and only if you optimize for value.
• Get the economic model right.. Many companies sell small-ish deals to large enterprise clients, meaning the sales cycle is long(months) but lacks the benefits of enterprise sales( size and scale)
• Hiring the right consultative sellers who can be Friends (ie. build relationships), Philosophers (i.e offer sincere value-based advice) and Guides (i.e. consultative comparison of options) are key to success.