About the author
Norwest CRO Operating Executive and Principal, David Rudnitsky, is a veteran revenue leader who helped build Salesforce’s enterprise selling motion from $23 million to multi-billion-dollar scale. His strategies and frameworks were documented in Marc Benioff’s best-selling book “Behind the Cloud” and continue to influence how companies approach enterprise readiness today.
Every organization with aspirations to be “enterprise-ready” has that aha moment. It’s when the awareness sets in that you may not be able to close and/or service your largest opportunity, even though all the buying signals are in your favor.
It’s not because your product isn’t good enough. It’s not because the pricing is wrong. It’s the realization that you’re running a startup playbook against enterprise expectations.
Before joining Norwest as CRO Operating Executive and Principal, I spent decades building enterprise sales organizations. Here’s what I learned: The deals that keep you awake at night aren’t the ones you lose to competitors. They’re the ones you lose to yourself. They’re the ones that you neglected to ask why you won’t win the deal.
The other lesson I’ve learned is that being “enterprise-ready” is a two-sided coin: how you act and how you sell. Enterprises are evaluating whether you can become the kind of partner they need you to be. And if your organization doesn’t signal enterprise readiness at every touchpoint, they’ll find someone who does.
Your first challenge is to stop thinking about enterprise readiness as a product problem and start seeing it as an organizational design challenge.
Enterprise customers buy systems. They buy predictability. They buy confidence that their strategic technology partner will scale alongside them, evolve with their needs, and never become their biggest operational risk.
Instead of asking “What do we need to sell this deal?” start asking “What do we need to become the company that consistently wins, retains, and grows these relationships?”
The answer isn’t just better features or more sales reps. It’s rebuilding your entire revenue organization around enterprise expectations.
The Five Pillars of Being Enterprise-Ready
1. Sales Architecture That Mirrors How Enterprises Actually Buy
As a Chief Revenue Officer (CRO) targeting the enterprise segment, your goal is to architect your sales organization to balance long and challenging sales cycles, complex integrations, and a high bar for trust and support. You need to rebuild your go-to-market motion around this reality.
This means creating specialized roles: hunters who open accounts, farmers who expand them, and overlay specialists who speak the language of domain, industry, security, integration, and compliance. It helps to organize territories around vertical expertise because a manufacturing company needs to solve different problems than a financial services firm.
Most importantly, you need to develop value-based selling frameworks that align with how executives actually make strategic technology decisions. Instead of leading with features, lead with business outcomes. Instead of answering technical questions, anticipate them.
2. Segmentation That Actually Matters
Most companies think segmentation is about deal size. It’s not. It’s about motion complexity.
Enterprise deals are fundamentally different from mid-market transactions. They involve longer sales cycles, more stakeholders, higher scrutiny, and completely different success metrics. You can’t run enterprise motions with mid-market processes any more than you can run mid-market deals with SMB tactics.
Segmenting your Sales and Go-to-Market (GTM) teams is critical to maximizing efficiency, tailoring messaging, and accelerating revenue.
Your enterprise reps should focus exclusively on larger accounts. They need different quotas, different training, and different support structures. This approach prioritizes specialization over hierarchy. And while your enterprise team goes deep on complex deals, your mid-market team stays focused on velocity.
Each segment gets the attention it deserves, and buyers get experiences tailored to their expectations and needs.
3. Customer Success as Your Secret Revenue Weapon
The lifeblood of any good SaaS company is the ability to renew and expand. The business takes off once your net renewals far outweigh new sales. That’s the inflection point.
Achieving a best-in-class renewal rate requires you to build a post-sales motion that’s proactive across all facets: onboarding, QBRs, health scoring, and executive alignment. Your job is to turn customer success into a machine for net dollar retention and upsell velocity.
Your CS team should prevent churn while identifying expansion opportunities, facilitating executive relationships, and turning satisfied customers into reference accounts that close future deals.
4. The Infrastructure They Never See (But Always Feel)
World-class enterprise software companies earn their distinction through a combination of product maturity and scalability to support tens of thousands of users with global uptime. They offer customization, extensibility, and integration depth via robust APIs, SDKs, App Marketplaces and low-code environments. Customer success and forward-looking innovation are built to serve complex enterprise needs across industries.
Can you efficiently provision new users? Can you integrate with their existing tech stack? Can you provide audit trails that satisfy their compliance requirements? Can you scale usage without breaking performance?
You need to invest heavily in “invisible excellence” — the systems and processes that enterprise customers never see but always experience. SOC 2 certification. Single sign-on. Advanced security controls. Robust APIs. Professional services capabilities. AI & infrastructure are rapidly becoming the critical differentiators for enterprise vendors.
5. Forecasting as a Leadership Discipline
Enterprise deals are complex, high-stakes, and unpredictable, all of which makes accurate forecasting both critical and incredibly difficult.
Precision forecasting builds confidence and control at scale, preparing you for impacts to headcount planning, board trust, cash runway, investments, and valuation.
I transformed forecasting from a reporting exercise into a leadership discipline. Every deal underwent rigorous inspection. Every forecast reflected multi-threaded relationships, competitive dynamics, and realistic timelines. My sales leaders had a great sense of pride in their ability to deliver timely and accurate forecasts. Every pipeline review became a coaching session focused on advancing specific opportunities.
It’s mission-critical to build organizational muscle around deal inspection, qualification, and advancement. Your sellers will hone their intuition around what makes deals winnable and what makes them risky.
The Mindset That Binds It All Together
Systems and processes are just the foundation. They are table stakes, but what really transforms good companies into enterprise-ready organizations is mindset.
Internally, this mindset shows up as discipline. Choose clarity over chaos and build habits that support sustainable performance.
Externally, it manifests as consistency. Every touchpoint — from the first sales call to the renewal conversation — reflects the same level of preparation, professionalism, and commitment to customer success.
As CROs, we have the opportunity to champion this transformation. It means institutionalizing a repeatable, high-velocity sales process, building customer-centric success teams, and pushing our organizations to invest in compliance, security, and integration capabilities that meet enterprise-grade expectations.
The companies that win at enterprise scale aren’t necessarily the ones with the best products. They’re the ones that build organizations worthy of their customers’ trust.
That’s the difference between selling to enterprises and becoming enterprise ready. And that’s what turns sleepless nights into sustainable growth.
