Who is this field guide for?

This field guide is designed for SaaS founders and sales leaders who are ready to tackle the enterprise market. If you've built a product that solves complex problems and you're eager to scale your outbound sales motion, this guide is for you. Perhaps you're seeing early traction with smaller clients but want to land those coveted six or seven-figure deals. Or maybe you're at the crossroads of deciding between a self-serve model and a high-touch sales approach.

Whether you're grappling with product readiness for enterprise clients, struggling to create social proof, or unsure how to build the right sales team, this guide offers practical insights. We'll walk you through the journey from identifying your ideal customer profile to closing deals and ensuring customer success. Let's dive in.

About Everstage:

Charlie Munger said, 'Show me the incentive, and I will show you the outcome'. Sales incentives are a major part of salesmen's compensations, varying anywhere from 20-50% (and at times even 100%). For most sales-led companies, both tech & non-tech, by this metric, sales compensation expense would contribute anywhere from 5-10% of the cost base. Incentives are a major tool for companies to implement their go-to-market strategies and push the sales team to achieve desired outcomes. However, managing these incentives can be a complex and time-consuming process, especially as companies scale and their sales compensation plans become more intricate.

This is where Everstage comes in. Founded in 2020, Everstage is a SaaS startup that specializes in automating sales commission processes for companies. The platform offers a no-code solution that enables businesses to design and manage complex commission plans, ensure accurate and timely payouts, and motivate sellers with real-time visibility and insights on their commissions.

First Things First: Why Enterprise?

Ask this question to an investor, and you will hear the following in some order :) high ACVs, lower churn & better retention and customer stability.

But in this context, let us look deeper at what enterprises stand for. Enterprises stand for complexity, at the very basic level. This complexity manifests itself in multiple forms: use cases, workflows, sales cycles, configurability, security, etc. Enterprises would ask for a sophisticated and deep product from day 1. Similarly, you might have to go in front of large buyer committees and think about multithreading sales conversations early on. This often results in longer gestation periods for product development & GTM execution - simply because it takes time to unpack this complexity. And very often tackling this complexity becomes a moat. If done well, you have a set of high-quality customers, which if served well will rarely churn or die and are highly referenceable.

0 To 1 Of Building An Outbound Enterprise Motion

Step 0: Is Your Product Ready?

To sell into enterprises, your product needs more than a broad set of features. You need depth of functionality to support the complex use cases and workflows of large organizations. Enabling extreme configurability is key, as enterprises will have unique requirements you can't anticipate on Day 1.

Invest early in security certifications like SOC 2 and enterprise features like SSO, RBAC, and audit logs. Tools like EnterpriseReady.io provide a helpful checklist. Everstage was SOC2 compliant before it launched. Avoid making assumptions about enterprise requirements. Be prepared for edge cases and unique demands.

As Siva shared: 'Enterprises can quickly humble you. They'll throw use cases at you that you could never imagine.'

Step 1: Understanding Product Category & Persona

Here are a few questions founders need to answer, which will form the basis of many decisions as they think about building the right GTM:

Is your category already established?

Who are your competitors - and what are the major gaps in the experience?

Do you have a ready market to go after or will you be required to build the problem and solution awareness?

Is the intent to buy or the pain point being expressed somewhere already?

Who are the key user & buyer personas for your product?

Where are they aggregating, and what are they consuming & expressing there?

What is the persona’s pain? Can you classify the pain into softer personal pain (eg: unable to think of a career path) & frustrations linked to the product?

Once you have answered these questions in detail, the next step is to start creating legitimacy/recognition for your product & brand.

Step 2: Create Social Proof & Recall For Your Product

Enterprises need to establish legitimacy before they buy. A more extreme expression of this sentiment lies in the phrase “No one ever got fired for buying Salesforce”. If your product is in a critical, established category, the incumbent has this huge leg up at all points of time - they are the safer option.

So you need to establish social proof and give your buyer the backup and strong reasons to unseat the incumbent or the better-focussed competitor. At Everstage, from the early days, they focused on building our presence on forums where our buyers and users spent time. G2, Capterra, and TrustRadius were often the first places our prospects went to when they had to look for a product. Building a large body of reviews (and delivering an experience that ensured customers wrote positive reviews :)) helped us immensely. Within 8 quarters of launch, Everstage was rated as the best Enterprise Sales Compensation Management platform globally by G2. Furthermore, Siva’s experience as a RevOps leader, helped them get over the hump of vintage. In the early days, Siva being a part of deals ended by being a big differentiator.

Secondly, you need to build recall & recognition for your product (and team). This entails writing thought leadership pieces, organizing webinars & events, building a social media presence, etc. But again, the characteristics of the persona need to be kept in mind. For example, Everstage decided to focus all (or most of it) its social media strategy on LinkedIn, which is where RevOps & Finance folks spent most of their time. Similarly, they focused their content heavily on career progression for RevOps folks (and a little on the product), often co-created with senior RevOps leaders - career progression is a deep pain point for this persona, given Operations is a rather non-glamorous persona.

Step 3: A Couple More Questions

How would I like the customer to experience my product? should i go self-serve/trial-led, or should I go to a sales-heavy model?

It depends a fair bit but a general rule is to decide this on the basis of what it takes to deliver value to the customer. If it is a complex product, where value creation & demonstration takes time, it is almost always better to ensure that the sale & product experience are assisted by the sales team. Secondly, if the buyer journey is complex, where the buyer & user persona are separate, and the budget allocations will require approvals, it is better to establish a more direct connection with the customer. For Everstage, both of these arguments were true. Siva envisaged that showing value in an established category will require not only an involved selling journey but very often a POC. There will be multithreaded conversations, involving multiple stakeholders as well.

What if the competitors are providing a self-service experience, but my gut says otherwise?

Everstage so far has not run into this conundrum. But the answer to this question is more nuanced. First of all, we have to be absolutely sure that the competitors are solving the same problem statement for the same segment of customers. It may be likely that the competitor is catering to a more down-market segment. Secondly, if the customers value the self-serve part and that is making a material distinction in their choice to buy (this will manifest in a higher number of qualified leads, better conversions, etc for competitors). Additionally, self-serve channels often have a lot of noise, so if one needs to sell extensively after self-serve, it will require extensive qualification, and often at early stages, companies do not have enough bandwidth.

Step 4: Set Up Your Outbound Motion

Multiple types of outbound: cold call, intent led, ABM. Cold calls and emails, while effective at times, often are unscalable. Cold calls especially are people-dependent (you might have a great sales rep killing it, while others might not). You might reach out to people who are not even problem-aware. Secondly, outbound sales should not be thought of as independent of inbound marketing. Outbound augments inbound and strong inbound marketing solves for both problem awareness and product awareness, thereby pushing your conversions up.

In established categories, intent-led outbounds are a good way to qualify for problem-aware leads, who are actively looking for solutions. There are a bunch of data providers who will provide you with this intent data. That is where Siva started.

1. The first substep here is to identify these partnerships/tools to get this intent data (for example, a bunch of your prospects might be coming to your G2 page or website but still might not be clicking). These are high-intent but not as qualified leads.
2. Next figure out how best to mine this data. This data can be enriched by using multiple data providers. Identify your ideal customer profiles from this data.
3. Additionally, in Everstage’s case, a lot of time was spent ensuring data quality. Further, enterprises generally (and RevOps in particular) often have creative titles. These titles might vary across sectors and tenures. It is advisable to have a combination of a RevOps and a marketing associate spending enough time to ensure the quality of the data. Build a 360-degree view of the accounts (revenue potential, tech stack, etc.).
4. Start writing the emails. A lot of time should be spent getting this positioning right (50% of the email is in the subject line:)). Over time, you will be able to develop personalized messaging for your account and the persona.
5. You should be able to track the funnels well and be confident about the quality of data (otherwise, all of your experiments will be GIGO). Implement enterprise-grade systems across CRM, sales enablement, conversational intelligence, contract management, and BI. Track metrics across the pipeline—lead generation, opportunity conversion, deal velocity, and win rates. Monitor leading indicators of revenue—ACV, TCV, churn, and expansion rates. The role of RevOps hire is extremely critical here.
6. Think long and hard about your deal funnel. Apart from closure what are the other milestones you want to track - this is critical in situations with long deal cycles. For Everstage, progression to POC was a key metric and a good leading indicator. After the first sales call, share a mutual action plan with timelines. Get your champion's sign-off, and hold everyone accountable. Identify and engage all key stakeholders - economic buyers, decision makers, influencers, and users. Multi-thread and get their buy-in early.
7. As you identify specific verticals where you have established playbooks to sell and are seeing a pull for the product, it will be time to set up account-based marketing motions to expand your lead pool. Referenceability is a big driver of conversion rates.

Step 5: Building The Right Sales Team

RevOps and marketing ops & research are two roles one should definitely hire for early. Further, at the early stages, it is better to hire experienced BDRs, who are self-starters and motivated and set up the customer outreach. Whether to hire the BDR in India or the US continues to be a point of contention. India offers a cost advantage, while the US has a great depth in talent pool. Companies planning to do so need to invest in a good BDR training function as a lack of talent pool will be a bottleneck in later stages. Everstage has been able to build and scale a BDR team in India and has started seeing early success with fresh BDRs.

Your VP of sales will often be the first expensive hire in the US ($450-550k OTE). 90% of the first VP of sales leave in 6 months - and this sets the organization back by at least 9-12 months. Before hiring a VP of sales, we need to ensure the following:

a) Predictability in pipeline generation and some pipeline maturity: Without this, the VP will find it extremely difficult to get early wins and will not have a line of sight to fulfilling their quota. A good thumb rule can be to hire the VP of sales only after the company has closed the first million in sales. The founder should ideally play this role until that point.

b) Look for someone who is willing to be extremely hands-on. Domain expertise is important, but I would index on the ability to be hands-on more. This is because the first VP will need to design your sales process along with the AEs (and not just manage the team).

c) Do as many reference checks as possible. Sales people can sell themselves, so references can be a good way to validate their management style.

Step 6: Make The Customer Massively Successful

Closing large deals is only the beginning. You need to deliver an exceptional customer experience to drive adoption, satisfaction and loyalty. Have a smooth handoff process from sales to dedicated customer success managers (CSMs). Arm your CSMs with a deep understanding of the customer's goals and success metrics.

Recognize the value of offering professional services strategically. Many successful enterprise SaaS companies initially derived a meaningful portion of their revenue from services. It allows you to gain deeper customer insights & context and generates cash flow in the early days. It differentiates you from competitors who outsource services to third-party agencies and keeps you closely connected to customer needs.

Conclusion

In conclusion, building a scalable outbound motion for enterprise SaaS requires a thoughtful, multi-faceted approach. By focusing on product readiness, establishing social proof, implementing a robust outbound strategy, assembling the right sales team, and ensuring customer success, founders can lay the groundwork for long-term growth and success in the enterprise market. While the journey may be challenging, the rewards of serving enterprise customers—high ACVs, lower churn, and strong customer relationships—make it a worthwhile endeavor for many SaaS startups.