Best Practices & Lessons Learned

Sales Readiness (incl. success, support, & services)

• Have clear segmentation on which accounts are ENT. Have a clear plan to transition accounts to ENT AEs; otherwise, existing account owners will fight tooth and nail to hold the best accounts.
• Do not leverage your existing SMB focused team (SDRs, AEs, sales engineers, marketing) to sell ‘part-time’ to the enterprise; that is a recipe for failure Instead, spin up a dedicated team with enough critical mass to succeed.
  • Some, if not most, of your ENT tiger team should be drawn from existing high-performers who have closed high-ACV, complex deals. You’ll need to keep them whole compensation-wise for at least the first 12 months.
  • If you do not have existing high-performers who have closed high-ACV, complex deals to promote or you cannot afford the risk of promoting them, then hire ENT reps from the outside. This significantly increases risk and must be done with extreme care. Big company reps tend to not adjust well to the scrappiness needed to stand up a new segment. Instead, target hunter AEs who have sold similar solutions to similar companies at similar price points.
• The first line sales manager of the ENT team is perhaps the hardest to fill. Ideally, this should be a leader on your SMB with (strong) prior experience with enterprise sales. If you must hire from the outside, as with hiring outside AEs, you want someone who has lead teams selling similar solutions to similar companies at similar price points. This person must be very disciplined in defining the sales process and inspecting deals to hold reps accountable. They will very likely act as a player/coach.
• Expect to enter with a land & expand strategy. This will often start with an (unpaid) pilot or PoC.
• Often the enterprise will already be using an incumbent system. If possible, enter with a feature (wedge) that allows you to gradually replace the incumbent.
• You’ll need robust implementation, customer success, and professional services (large enterprises expect to outsource onboarding, training, etc.); you may support this directly or via channel partners
• Expect more complex negotiation and legal red lining. You need to know the ‘norms’ for enterprise contracting.
• Set criteria for whether or not you will respond to RFPs. If you will, then identify who owns the response. Few AEs are skilled at this; usually it is handled by a deal desk or sales engineers.

Marketing Readiness (incl. demand generation)

• Refine/narrow your ICP – geo, industry, specific size range, technographics, etc.
• Identify marquee / target logos that fit your ICP and pull out all the ABx stops to acquire them. Once you win these logos, ensure they are featured prominently in every aspect of your marketing (website, blog, podcasts, etc.). You are what you look like — if your marketing ‘looks and smells’ SMB, then that is what you are. Project ENT if you aspire to be ENT.
• ENT demand gen, especially in the early days, is an all-hands-on-deck team sport. This will likely require a decent amount of CEO/founder-led selling to get things started. Marketing can soften the beaches but one should not expect ENT inbound unless you have a PLG motion. Cold outbound from SDRs and/or AEs is very unlikely to work.

Product & Engineering Readiness (incl. pricing & packaging)

• Start with a sprint to assess product market fit (PMF) and the competitive landscape in the enterprise. This will help identify many key gaps and tighten up your messaging.
• Expect that your product will need to evolve to serve large enterprises so ensure you have carved out product management and engineering capacity in advance. Some key considerations:
  • Enhanced security features
  • International data centers
  • Role & permission framework to support separate workspaces (ex: to ‘ringfence’ different business units)
  • Support for multiple languages
  • Interoperability / integration with complementary systems
  • Certifications (ex; SOC 2 Type 2)
• Be ready to adjust your pricing & packaging; this may require a switch to active user or usage based pricing
• Avoid sweeping “enterprise agreements” that prevent your ability to expand in the future

General Readiness (other functions)

• Expect the move upmarket to easily take up to 2 years to get right. Fund fully (or don’t do it) and be patient.