Feb 26, 2019
Connecting Security, Technology, Leadership and Sales with
Guest Mike Kail
Mike Kail is the CTO of Everest.org, with over 25 years working
in technology companies from large to early-stage
We discuss Security, SecDevOps, Sales and Software Development
Alignment, Sales Rep Outreach, Compensation, Leadership, Focus,
etc. This discussion crosses a number of different critical
areas that will impact your organization.
Thank you Mike for joining us this week - the discussion was
- What are some lessons Mike learned as he has become more
experienced on the sales side of the equation?
- Why do sales reps forget empathy?
- If Mike's working with a vendor, what are some questions a
rep can ask to reveal timeline, focus, plan?
- How often does Mike delegate research to other members of
the team? Where does collaboration fit?
- How can we build better rapport?
- How often does Mike see the same type of outreach
- What is DevSecOps?
- Why do people worry about security teams in the
- What Leadership traits are necessary in successful
- How do you create better alignment to support the building
- Technical founders tend to focus on the how.
Alternatively, focus more on the why, the business problems that
- Maintain a partnership vs a hands-off relationship.
- It is difficult to read the context.
- Hope and desperation fuel sales tactics, this is never
- Layout the "Why Strategy" on a proper timeline.
- Spamming and hoping something sticks does not work.
- "Don't make your problem my problem" - Mike
- There is nothing magical in the end of quarter
- Questions to consider.
- Is this tied to something larger?
- What are the side-effects?
- Who are the cast of characters?
- How will this impact the business?
- Ask questions, set expectations.
- Establish communication protocol sooner rather than later.
- Play poker - learn how to read tells.
- Transparent conversations are important, build relationships,
- Be personal, do the work.
- If you are going to send canned messages - remember to
- DevSecOps - helps to make security a first-class citizen.
- There has been a shift from control based to more
- Sometimes security is perceived as a weapon. In less
forward-thinking orgs it may be perceived as a checkbox.
- Involve security early in the discussion.
- The security team does not need to be software engineers,
but they need to understand how security impacts or should be
considered in the pipeline.
- Software engineers should be aware of security hygiene.
- Culture of transparency, open communication, empathy, are all
important. You can't play the blame game.
- In a disagreement, take the position of the other person,
start solving problems, and not worry about who is right.
- In many organizations, the sales data is about reporting up,
and does not include context.
- Design is important in security, operations, and sales.
- Empathy - in the DevOps world you have a post mortem, which is
blameless. Think about how this can apply to your sales
- Post-Mortems - there is value in having them not be
- Two foundational leadership traits - Trust & Respect
- You are on the same team.
- Identify your north star, and remind people of that.
- Everybody is human.
- Early technical founder - trying to improve sales - focus on
the why, the value proposition, the business impact.
Call to Action/Engagement Question
- How are you taking an operational oriented approach to your
- Think about how you can apply the post mortem in your
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