The First 100 Days – When a New VP of Sales or a CRO Starts

I was recently asked what a new Sales Leader should do during their first three months (i.e. the first quarter) at their job.  And just the other day, I saw a link from SBI posting a video where Matt Sharrers (the CEO of SBI) asked Eric Vermillion (a former CRO of BlueCat) about what happens when new head of Sales starts – see this video here: “A Quick Start Guide for New CROs“.

Eric mentioned the following in this video (my notes on the couple of steps that Eric discussed):

  • Don’t be the “anti- guy before me” – don’t start your legacy by saying what a louzy job the prior executive did and don’t criticize them. Focus on building your own legacy and learn the good things they did before.
  • Listen, learn and build a plan. Don’t bring in the slide decks from your last place and just replace the logo – every company is different even if it looks similar.  You need to build a plan that is relevant to your new organization at this time and place.
  • Create a roster of the top deals that you can personally impact and help deliver yourself (not necessarily the biggest ones on the rails but the ones you can help with)
  • Have a level of transparency with the rest of the organization and build a good story with everyone about their involvement and what you expect in terms of helping sales with deals. Get the rest of the company behind you and get them vested in the success of the sales organization.  Your success is the byproduct of the buy-in that the rest of the people have.

I really like what Matt and Eric discussed and also wanted to share some of my own thoughts on this topic.  I think of starting a new role as the “First 100 Days” which applies to U.S. Presidency and equally applies for a VP of Sales or a CRO (or a CEO or any C-Level for that matter).  Here are a couple of steps in the process for the First 100 Days that I want to share:

  • Listen, Observe, Learn (and then listen some more)
    • Remember that “Prescription without diagnosis is malpractice” – first seek to understand what is happening rather than instantly prescribing any changes
    • Do not act impulsively on what you learn or hear – keep listening and learning
    • Seek to understand before seeking to be understood
  • Show Respect for the Existing Culture, History & Legacy
    • respect the existing culture and the people who have invested previously in the organization
    • don’t rush into making any changes right away before you really understand and listen
    • be supportive and respectful of the legacy of the organization in all communications with everyone
    • as Eric Vermillion discussed in the SBI video, don’t criticize the previous VP – it’s unnecessary, not tactful & sets a bad precedent for your team
    • also – while you will begin to instill your own systems, decisions, processes and, of course, sales team “Principles/Core Values” as well as Sales Culture, you need to first ground that in respecting the history before you earn the trust and the right to show why you can introduce something new (i.e. it should end up being a smooth and logical transition rather than an abrupt one that ignores and doesn’t respect what has already been working or been put in place and followed historically)
  • Primary Focus on the People & Team
    • The overarching focus is on “Organizational Health” during this period
    • People focus is the #1 priority – a business is only as good as its people
      • Spend 90% of your time with people – most of your time should be focused exclusively on the people
      • Be present and ensure you earn trust of your new team
      • Build bridges and new relationships
    • Introduce yourself to the sales team and other groups
      • Do a sales team weekly kickoff with an Open Q&A
      • Communicate your intentions to listen, observe and learn
      • Do a casual meet & greet for the team to get to know people outside of work
      • Ensure everyone feels comfortable coming to you with any questions
      • Meet other groups as well including Marketing, Customer Success, Product, etc.
    • Also, ask the existing team for their feedback
      • Invest in 1-on-1 time – ask what’s working and what’s not working
      • Be Open-Minded to everything you hear and learn from the existing team
    • Create your “unofficial team” of Trusted Advisers
      • aka “Guiding Coalition” –  trusted allies and stakeholders in managing the change period
      • internal influencers who help you oversee the success during the transition and beyond
      • a leader needs a team of willing and trusted people – successful transition is a team sport
    • Team Development
      • this is one of the key fundamental steps to do immediately to ensure ongoing sales productivity
      • ensure that there is ongoing development to ensure to continuously level up the team
      • every sales team in the sales group should have a process for sales coaching and ongoing training
      • every FLM (Front Line Manager) should have a “coaching plan” for each of their reps on the team
    • Recruiting with an eye towards the future
      • Create a Skillset Matrix – assess what skill gaps you need to fill
      • Build a capacity model and design a People / Recruiting Plan
        • If needed, recruiting world-class A-players is critical (it’s a continuous process – i.e. every day is a Draft Day)
  • Clear & Open Communication
    • Remember that this can be a stressful time for the entire sales organization and the people don’t know what to expect
    • Communicate your high-level vision and strategy for the long term (do not imply any short-term changes)
    • Communicate your core values and principles even if you don’t yet formally implement them
    • Always “over-communicate clarity”
    • Focus on how your actions and words can impact others before you say or do anything
    • Be intentional in your communications and even in body language
    • Avoid and disincentivize any gossiping or complaining
    • Remember that your actions speak louder than words
    • Be proactive and not reactive in your communication and clarity
  • Sales Execution
    • As a VP of Sales / CRO, focus on helping your sales team achieve the sales quota
      • Your primary job is to make the sales team more successful and produce results
      • But you can hit the ground with closing some deals which brings us to the next point…
    • Roll up your sleeves & sell
      • Be more of a player in the “Player / Coach” context
      • Help sell new deals (usually at smaller companies you’ll do that right away)
      • Help your sales reps close some of their deals – help bring a few deals in
      • You can start with some existing leads or prospect for a bigger strategic deal
      • If you sell then it’s a great way to dig in, learn and understand as a VP of Sales
    • Culture of Accountability – it’s all about performance, execution and accountability
    • Create a sense of urgency to keep executing and hit the sales targets
    • Empower your team to be action-oriented and to have autonomy to execute
    • Generate “short term wins” in the first 30 days and over the span of 100 days
    • Transition is a critical time – ensure that your team is focused on execution
    • Reduce and mitigate any disruptions during the transition period
    • Ensure the team is focused on the High Payoff Activities (HPAs)
    • Keep an eye on Sales KPIs/metrics and leading indicators regularly
  • Pipeline 
    • Pipeline health – a healthy pipeline is key to ensuring the sales force makes the number
    • Ensure that an effective Pipeline Management process is in place
    • Review the pipeline metrics regularly
    • Win/Loss – Why we win, why we lose
      • carefully review lost Opps (even if qualified out) – what are the loss reasons, why do we lose
      • understand why deals are typically lost as this is an important factor going forward
  • Customers
    • It’s important to introduce yourself to the customers
      • start with the select strategic customers
      • introduce yourself to new recent Customers
      • join on the phone with prospective Customers to help close the deals
      • you should try to meet in person with key and strategic customers
    • As soon as you can, begin of becoming real friends with 10 Customers
      • this will help you get to know them really well
      • will help you build true relationships that are valuable to the company
      • don’t just get to know the business side, become real friends
    • Understand the customer pain points and how your solution helps your customers
    • You should also be helpful to your team when needed to finalize a sale with new customers
  • Process
    • Process drives outcomes
    • Make sure you have the repeatable, predictable and consistent process
    • Talk to Customers and understand their buying journey to make sure the sales process matches the way they want to buy
  • Quick Audit – “The State of the State”
  • Finalize the the “Phase 1 Plan“
    • Before you accepted the job, you should’ve showed and socialized with the CEO a 100 Day Plan or “Phase 1 Plan”
      • At that stage it would be more general, focused on bigger picture
      • Would include your general Summary of Expected Achievements, Sales Goals / KPIs, high-level People Plan, etc.
    • And now you need to review it again, tighten it up, plug in the numbers, add new “knowns” and share with the CEO
      • Also think of it as a “30-60-90 Plan” (i.e. first 3 months) but under the banner of “The First 100 Days“
      • Establish the process for value creation and name the roles and responsibilities of the Guiding Coalition
      • Establish the “small wins” milestones and more concrete goals for each month
      • Communicate the plan to the executive team and the Sales group
  • Alignment
    • ensure there is alignment with all the key stakeholders and groups that help enable sales success
    • make time to have a 1-on-1 with all your peer executive VPs in the company during the 2-4 weeks
    • work closely with Marketing to gather the process of lead generation and pipeline creation for the sales team
    • work with the Product team and understand the release timelines and the process of their work with sales
  • Also: only *when and if* swift action is necessary – on rare occasions there are times when a new VP of Sales or a CRO starts out needing to make a few immediate decisions combined with swift action in the first 30-60 days – but this should be done very carefully by considering the impact on the organization and its people and always with thoughtful input of key stakeholders, starting with the CEO and other executive team members based on carefully collecting facts and information

What else? What are some other thoughts on a quick start?