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Adam Wainwright

AMA: Cacheflow GTM Team, Adam Wainwright on Influencing the C-Suite


April 30 @ 10:00AM PT

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  1. How do you ensure alignment when you have two senior executive stakeholders who disagree with each other on the proposed strategy and you are stuck in the middle?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Alignment is the name of the game. And yes, Sr. Execs aren't always seeing eye to eye. The good news is that Sr. Execs understand the unifying language of alignment. In other words, try to figure out, in independent settings, how your proposed strategy serves the bigger picture. The strategic initiatives. Maybe they are around revenue growth or operational efficiency, or just getting things to work the way they should. In any case, your goal is to build a consensus that your proposed strategy di ...Read More

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  2. Who do you align yourself with to gain momentum in the leadership organization?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    It's critical to figure out who the "fox" is at your business. The "fox" is that person who usually speaks a little bit slower in sr. meetings. Is the person who often other Sr. execs ask questions or seek insight. Foxes know whats going on with the needful. They control outcomes. Often CEOs will outsource big decisions to the "fox" Knowing who this person is is the hard part. But if you can find a "fox" you can slowly work with them, earn trust, and become a vital part of the decision tree. Fin ...Read More

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  3. What are the best habits to do when working with C-Suite?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Consistency is key - to an executive, stability, consistency, and a clear tenacity/lean-in are what will separate you from your colleagues. Habits include: Being early to the office when applicable Putting in that extra push in the evening -- when it works and if you have the time, giving a little extra is something that often gets rewarded in my experience. Being early on virtual calls (ie. all hands where the C-Suite is present) Ditch complaining. -- Understand the language of "problem stateme ...Read More

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  4. How did you work with the C-Suite, earlier in your career?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Early in my career, I made mistakes but when things started clicking, I moved up the ranks pretty quickly. Here are a few things I did to ensure the job I wanted was mine when it became available. Show up early, be available, and say yes when power people are watching - I literally turned the lights on in the office every morning for 4 years. I was always there and always available for risky projects when the C-Suite was building a thesis around something (in my case - for GTM) Be the tide that ...Read More

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  5. How do you influence the C-Suite to get more resources?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Influencing the C-suite happens in small settings. Depending how close to the office you are is corollary to how direct you can be with your resourcing request. When you get a chance to make a case, in a small setting, make sure you: Know your domain well. It's paramount that you truly understand the depth and breadth of your scope of responsibilities so you can observe these responsibilities from different lenses external to your domain. Know how your resource request drives/ impacts the big in ...Read More

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  6. What do your interactions with the C-Suite look like on a regular basis?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Brief, Bright, Gone. Everyone should read a book called "Cut to the Chase: and 99 Other Rules to Liberate Yourself and Gain Back the Gift of Time" by Stuart Levine. Execs speak in terms of big-picture ideas/moves. Brevity is key to engaging with the Exec Suite. You'll know where someone sits based on their ability to speak in terms of strategy, broad strokes ideas and their implication to the business versus more tactical, deep-on-detail concepts/problems/projects/responsibilities Generally spea ...Read More

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  7. What are some ways that junior and newer sales professionals can get greater exposure to the C-Suite?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Small spaces. The best way to get exposure to your C-Suite is to find where they are and create reasons to be there. This is a common sales practice. That is, do your homework. Figure out where you can cross-paths with your C-Suite and use an opportunity to broker an introduction if one hasn't already been made. Depending on the personality of the person you're trying to get in front of, you should be trying to learn 1 or all of the following things. Do they have an open-door policy? Do they hav ...Read More

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  8. How do sales key stakeholders from other departments change as your company grows?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Like anything, as a company grows, priorities change. It's hard to say how Key Stakeholders from other departments change (in this example) but in every growing business I've ever been a part of, what really matters is alignment to the mission. If Stakeholders' roles are impacted because the mission is evolving, this is where you'll see big moves or changes across the stakeholder landscape. Stay close to the stakeholders who have a clear understanding of the mission, and make sure its the same m ...Read More

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  9. What are the top 3 things that will provide value to C-Suites as a sales leader?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Hitting the number is the first thing - But this wasn't all that easy to do over these last few years, so here are some things that will provide value to the C-Suite as a sales leader. Keeping the troops aligned to the big picture -- Keeping the team engaged, happy, and focused on the big picture is exhausting but rewarding. C-Suite will pick up an unrelenting positive outlook and will reward sales leaders when applicable Organizing feedback loops from the field to the C-Suite. The C-Suite is al ...Read More

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  10. What do sales leaders get wrong when trying to influence the C-Suite?

    Adam Wainwright
    Adam Wainwright

    HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • 2y

    Sales leaders always get this wrong - that is, they typically say something like:

    "I know everything that this role requires ... do it my way." - Every Sales Leader

    A great sales leader has an informed point of view, but a whole hell of a lot of humility and willingness to adjust, massage, pivot, lean in, etc.

    Bad sales leaders over quote non-senes sales mantras -- Great sales leaders get on calls listen to reps dealing with tough situations in deals, and ultimately help the business win.

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