What are the biggest surprises when going from a company where sales was established to one where you have to establish sales?

You have to have a glutton for punishment moving from structure to no structure, take it from me, but it can be such a rewarding and fulfilling experience to build something from 0→1. Throughout my career, I wouldn’t say there have been many surprises, moreso ‘opportunities’ to put a positive spin on it.

Systems & Reporting: We forget how easy we have it being at a larger organization where you have countless resources for technologies that have already been vetted and rolled out, and full funnel reporting to support pipeline/revenue trends, forecasting predictability, etc. 

• My advice for any revenue leader starting from scratch is to bring in a RevOps hire. This is the most critical investment you can make to build the foundation for your revenue motion. 

Market Positioning & Value Prop: Don’t expect a clear deck with clear customer case studies, ROI metrics, customer facing collateral, competitive positioning, discovery questions, pitch scripts, etc. As the first sales hire, you must build this. 

• My advice: Customer tour of duty. This is your opportunity to connect with customers to understand how they use your product, what’s resonating, what needs improvement, etc.

Pipeline: You likely won’t have a marketing engine generating inbound leads, let alone an outbound engine targeting key accounts that have high propensity to engage with you.

• My advice: Partner with RevOps to understand your target audience by:

  • Defining your ICP: company size, industry, revenue, geographic location, and technology stack

  • Leveraging Data: CRM, historical deals, and win/loss analysis, inbound analysis, etc. to find patterns in successful accounts

    • Intent & Firmographic Data: Third-party tools to gather intent signals (hiring, tech stack, funding, ICP profiles, etc.) and firmographic information (company size, geo, industry, etc.)

Hiring: Do not rush this. As the first sales hire, you should be running every single deal for the first 30-60 days. Deeply understand your customers, their challenges, and how you can solve them. 

• My advice: You must fire “Full Stack AEs” who have something to prove and are willing to hunt, convert, close, and expand. Bring on talent who can do it all. Less is more and remember to hire for the innate skillsets that you cannot teach: grit, humility, curiosity, high EQ, perseverance, hunger, etc.

Product & GTM Alignment: This is one of the most critical relationships to get right if you want to grow your revenue engine.

• My advice: Create a shared vision with Product and how you plan to differentiate in the market. Create a consistent and clear feedback loop between you and your revenue team and Product where you sync often to understand which key features, workflows, and customer requests would impact the most ARR if rolled out. Communication is key, but ensuring you cut out the noise from one off feature requests is most important. Decisions should be made in a binary and objective approach (ARR).