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Best of War Room AMAs

Discover top executives' preferred methods of being sold to, as told by the executives themselves in our compilation of the War Room AMA series.

We’ve established that Bravado Academy is a place to come for anyone to get top-notch sales content. But for those of you not already in the War Room, you may be surprised to learn that we have another wildly useful source of powerful information: War Room AMAs, aka our exclusive “Ask Me Anything” series where we ask top execs from leading organizations to enter the War Room and let members, well, ask them anything.

Here are our favorite snippets from each of our AMA guests:

To read the full thread in the War Room, just click on the links at the bottom.


Robert Knoblauch - Deputy CISO @ Scotiabank

How often do you reevaluate security policy? I often find CISOs I sell to are reluctant to evaluate new tools if they don’t meet some predetermined criteria. For you - what normally convinces you to evaluate new tech?

Not specific to my company, but in the form of best practice - regulatory policy tends to drive cyber policy. Also best practices change over time, also changes in technology - SaaS and Cloud being good examples of having to re-tool; and incorporate new policies... it's a significant change in technology.

Another example is change in waterfall vs. agile development; it requires a different approach from static code scanning to CI/AD integrated security vulnerability management.... however I find that often the core policies and logical models don't change much over time... one simile to drive the point in banking is back in the wild west it used to be a physical vault, now it's a vault of 1's and 0's... but the same concept of who holds the keys, how is the access control done, etc...fundamental concepts still applicable today.

The short answer is often it is regulatory drivers and also real-world incidents/examples. Everyone is really concerned about Ransomware, and to prove how this co-exists with regulations - both NIST (USA) and UK Government have issued really impressive guidance on Ransomware resiliency.

If you’ve considered purchasing a product/solution in the past but didn’t purchase it in the end, why?

Happens all the time, big bake-off, PoC's, 6-12 months of eval to end up not purchasing.

The biggest reason is the solution didn't do what we needed it to do, second is an existing vendor has created the same functionality in an existing product (happens a lot) and also the eval team (ie: people who will end up running the technology) feel it's not worth the effort (operationally complex) or something better is coming down the road.

One example of this particular problem is comparing on-prem solutions to SaaS solutions... would you run your own email system in-house or use office 365? Ask that question 10 years ago and you would have a different answer.

James Shen - Head of Corporate Finance @ Gitlab

When a team at GitLab comes to you with a request to allocate budget for a new tool or service, what goes into your decision to approve/deny? Is there anything we as reps can add into the business case to sway the decision towards an approval for budget?

Three things to share:

  • Prove to me you’ve done your research. When a team shares in-depth research, it goes a long way, such as: benchmarking what our peers purchase, what comp transactions look like, what Gartner says about the space, etc. To the extent you have this data, share it with your buyer to arm them.
  • Think strategically and long-term about the solution. I am not thinking about a feature which solves a pain point today, but about how the solution fits with our company in 3-5 years. How does the vendor address our future pain points? What other areas are they branching into which we could use? Or does it get ripped out and replaced in a year?
  • Is the executive sponsor fighting for it? Keep in mind - finance doesn’t technically own the departmental budget after it is allocated during the Planning cycle, the business-unit exec does. If s/he believes in your solution, they will fight for it, and when push comes to shove a good finance team will support.

When would you say is the ideal time for a sales rep to get the finance team involved in the sales cycle? Do you prefer to be an active or passive member of that process?

It depends - for most purchases I like to be passive and can be brought in later. For major purchases where there are large financial obligations, I get more actively involved and would like to be involved as soon as pricing starts to get scoped.

Think of a good finance team as an advisor to your business unit during purchase decisions. The subject matter expert is the business unit, the budget is owned by that exec, and they live with the consequences of their purchase. Finance advises by pressure testing, building business cases, and ultimately providing approvals if the purchase is big enough.

But at the end of the day, the purchase decision is often owned by the business unit, not finance.

Camilla Velasquez - SVP Product @ Justworks

How do you go about evaluating an external solution when you're in the process of building a version internally? Is there anything from the sales side that we can do to make this comparison easier?

I want a salesperson to make me feel supported through the journey. It's obvious that something didn't go as planned, so I definitely don't want to feel like I failed - I want to feel like whatever I'm now buying can seamlessly integrate with the team that was going to work on this, and make them feel empowered and still in control.

So, something like "here's how we worked with existing teams to still keep them in the driver's seat and give them the control elements that building in the house usually gives you." I often find that building in-house is about control. We want the ability to do things "our way," so if there can be a win-win, that helps. All the control, none of the cost.

Why does it seem that product and sales are rarely on the same page? It always seemed to me that product rarely understands what actually closes deals and brings clients onboard...it seems there is a misalignment with priorities. Can you share the viewpoint from the product/engineering side?

In Product circles, we're taught that Product-driven growth is a long term play and looks something like this:

  • Build for defined customer target
  • Delight them like crazy
  • They sell the business on your behalf via referrals, positive reviews, etc

We're taught that "staying" features > "buying features" because in a fixed customer target set, these two sets of features are closely aligned, so why not work with the customers you have? Evangelical customers eventually sell on your behalf, which is the least expensive CAC there is.

I believe this to be true as a general principle if you have enough patience (which may not actually align with sales incentives, I understand). However, if (1) the above changes, then we have to work with the sales team to figure out how to even get to 2, and find the initial product-market-fit for that new segment.

Here's how this looks in real life as an example.

  • Leadership aligns and says, our target customer segment is tech and the size is midmarket.
  • Product teams find tech prospects in midmarket, and build something for them. These customers join, life is good for a bit.
  • Sales does their job and like the great entrepreneurs and tip of the spear you are, you find that maybe enterprise doctors can use this product and are coming into the lead funnel, and they get a little bit of traction, but relatively low win rate ensues. Sales team wants to convert existing leads so puts in a lot of requests.
  • Product ignores the requests because doctors and enterprise arent the target customer.
    Animosity ensues.
  • Eventually leadership comes together and says lets look through the data of low win rates, and now the customer targets are redefined, and a new cycle begins.

If the communication is low across teams with misaligned terminology, or the organization doesn't have an aligned leadership team on the target customer, this cycle can take a really long time.

General questions...

How do you feel about cold call vs cold. email outreach? Which have you found to be more effective?

Robert Knoblauch:
Cold Calling IMHO is the equivalent of going to a crowded bar and asking everyone, one after another for their phone number to get a date. It's low effort and low potential outcome. Email is slightly more effective because at least it goes to a folder in my inbox that eventually I will go through, usually during a very dry meeting that doesn't require my full attention.

James Shen:
Email is better by far. I give emails a passing glance before hitting Archive. The time may not be right, but if I need to research something later on, I may go search for an email I’ve seen in the past. I simply don’t pick up unknown numbers and rarely listen to VMs, which I mass-delete when my box gets full.

Survey says: EMAIL

What's one thing you want sales reps to ask that we miss?

James Shen:
Some of the most productive conversations I’ve had were after a sales rep asks me something to the tune of, “What gives you hesitation about moving forward?”

It’s an opportunity to move past the fluff and have an honest conversation about the blockers, which are what a lot of purchase decisions come down to. Don’t be afraid to dig. Also, don’t get too optimistic about any one prospect and not ask these types of questions. There are always things on the buyers’ mind - it is better to surface them proactively.

Robert Knoblauch:
I have never heard a sales representative ask me a really basic question: "What is the easiest way for me to work with you."

Camilla Velasquez:
Because I think similar culture and values are important for huge vendor investments, I'd want someone to suss this out:
"What can I tell you about our company or our values that might help to show how we're aligned or good fit to work together?"

I'm GitLab’s Head of Corporate Finance. Ask Me Anything
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I'm Scotiabank's Deputy CISO. Ask Me Anything
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I'm Justwork's SVP of Product. Ask Me Anything
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