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What are red flags when taking a Head of Sales role that should make you consider leaving within your first 90 days?

Tim Britt
Tim Britt
Freshworks Senior Director of Channels EuropeApril 11

When taking on a Head of Sales role, certain red flags may emerge within the first 90 days that could indicate challenges or issues within the organisation. While every situation is unique, here are some red flags to consider that may warrant reconsideration of your position:

  1. Lack of Support from Leadership:

    • If you encounter resistance or lack of support from executive leadership in implementing sales strategies or initiatives, it may signal broader issues with alignment or commitment to sales objectives.

  2. Unclear Expectations or Objectives:

    • If you find that expectations for the role are unclear or constantly shifting, it may indicate a lack of strategic direction or organizational instability.

  3. High Turnover in Sales Team:

    • If there is a pattern of high turnover within the sales team, it could be indicative of deeper issues such as poor leadership, ineffective sales processes, or cultural issues within the organisation.

  4. Inadequate Sales Infrastructure:

    • If essential sales infrastructure such as CRM systems, sales enablement tools, or support resources are lacking or poorly implemented, it can hinder the effectiveness of the sales team and impede growth.

  5. Misalignment of Values or Culture:

    • If you find that the company's values or culture are not aligned with your own, it may lead to dissatisfaction or difficulty in fulfilling your role effectively.

  6. Lack of Transparency or Communication:

    • If there is a lack of transparency or open communication within the organisation, it can lead to misunderstandings, mistrust, and challenges in executing sales strategies.

  7. Poor Financial Health or Market Position:

    • If the company is experiencing financial difficulties or is struggling to compete in the market, it may impact the viability of your role and the potential for success in driving revenue growth.

  8. Ethical Concerns or Red Flags:

    • If you encounter unethical practices or behavior within the organisation that goes against your values or professional standards, it may be a sign of deeper cultural or organisational issues.

  9. Overly Aggressive Sales Targets:

    • If sales targets are set unrealistically high or in a manner that puts undue pressure on the sales team, it can lead to burnout, turnover, and ultimately, poor performance.

  10. Lack of Opportunity for Growth or Development:

    • If there are limited opportunities for career growth or professional development within the organization, it may impact your long-term satisfaction and fulfilment in the role.

If you encounter one or more of these red flags within your first 90 days as Head of Sales, it's essential to carefully evaluate the situation and consider whether it aligns with your career goals and values. In some cases, it may be necessary to have candid discussions with leadership or explore alternative options that better suit your needs and aspirations.

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