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Dear SaaStr: What Are Some Tips For Shortening Enterprise Sales Cycles?

  • Tips for shortening enterprise sales cycles include hiring a VP of Sales with Enterprise Experience, getting good at pilots, asking about timing and budget early, understanding all stakeholders early, bringing in the CEO, specializing your sales team, embracing compliance early, running paid pilots or smaller deployments, showing up in person, and more.
  • A VP of Sales with experience can reduce sales cycles by months by navigating pilots, engaging stakeholders, and handling late-stage objections effectively.
  • Effective pilots with clear success criteria can accelerate trust and decision-making.
  • Prioritizing deals that are budgeted and have a clear timeline can help save time and resources.
  • Engaging with and selling to all stakeholders early can speed up the deal progression.
  • Involving the CEO in key conversations can help close deals faster.
  • Specializing sales teams according to deal size and complexity ensures the right level of attention is given to each deal.
  • Being proactive with compliance like SOC 2 can remove roadblocks that delay deals.
  • Running paid pilots or starting with smaller deployments can speed up commitment and build trust incrementally.
  • In-person interactions often accelerate deals in enterprise sales.
  • Although enterprise sales cycles are naturally longer, implementing these strategies can make them more efficient and practical.

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