Founders often over-prioritize non-revenue tasks like getting compliance certifications. Unless you are actively losing deals because you lack SOC 2 or ISO, you should delay it. View compliance as a task to be completed only when it becomes a direct blocker to sales, not as a box to check early on.
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Most new entrepreneurs wait for revenue before formalizing their business with an LLC or hiring an accountant. The savvier approach is to establish this legal and financial foundation from day one, even before profitability. This professionalizes the venture immediately, forces a serious mindset, and builds a solid base for future growth.
To avoid sounding pushy when asking critical questions about a deal's viability, frame them as necessary steps to ensure the customer's success post-implementation. This shifts the intent from closing a deal to building a successful partnership, encouraging open answers.
Don't treat onboarding as a post-sale task. Instead, actively sell the onboarding experience during the sales cycle. Introduce the implementation team and detail the steps to manage expectations, build confidence, and frame onboarding as a core part of the value proposition, not an afterthought.
Jumping to enterprise sales too early is a common founder mistake. Start in the mid-market where accounts have fewer demands. This allows you to perfect the product, build referenceable customers, and learn what's truly needed to win larger, more complex deals later on.
Founder-led selling is essential for the first 6-12 months but becomes a critical growth bottleneck if it continues. Founders who can't let go create a self-fulfilling prophecy where the business can't scale beyond them. They must be coached to transition from being the primary seller to an enabler of the sales team.
Enterprises are comfortable buying services. Sell a service engagement first, powered by your technology on the back end, to get your foot in the door. This builds trust and bypasses procurement hurdles associated with new software. Later, you can transition them to a SaaS product model.
Sales reps often become complacent when a deal enters its final stage, considering it "in the bag." This is dangerous, as this is precisely when unexpected hurdles from procurement or legal emerge. The "Red Zone" requires heightened focus and preparation for challenges, not premature celebration.
