Bill Macaitis has been SVP Marketing of Salesforce, CMO of Zendesk and CRO/CMO of Slack. He is currently a Board Advisor for aspiring unicorns and decacorns.

The Q&A Session with Bill was held on December 5th, 2018. This transcript has been edited for punctuation, grammar, etc.

Hello everyone, feel free to shoot me any questions. Happy to answer! I’m the former CMO/CRO of Slack, CMO of Zendesk and SVP Marketing of Salesforce.

Hey Bill, when to actually start with paid marketing?

I think you always want to have product market fit first before you really ramp up the paid media spend. Ideally, you will have built some momentum via organic channels first (word of mouth, content, PR, viral, etc.).

How’d you go about building the marketing strategy for Slack?

I was honored to be the first marketing hire there, coming in as the CMO. I think every company is different and you can’t apply a set playbook. That being said, I wanted to build a strong iconic brand and couple that with a sophisticated marketing tech stack that would allow us to scale fast. I always start, though with the marketing ops first … you need to have a strong foundation of analytics and the right tech stack to analyze how you are performing across funnel, brand and experience metrics.

Where do you see communication going outside of voice commands?

I think there still is a huge amount of rote work we do that can be automated via AI and smart integrations. Expense reports, calendaring, workflows and approvals are just a few of the areas that can be better automated and integrated into Slack to give you some time back in your day.

In a lot of ways, the amazing momentum that Alexa has built is similar to Slack. They both are a conduit for a countless number of integrations designed to make your life easier and more productive.

Is there a growth hack/tactic you recommend for startups?

I love sophisticated marketing tech stacks that allow you to do things like predictive lead scoring, multi-touch attribution, multi-variant testing, heat map analysis, etc. It all starts with a strong foundation of the right tools to allow you to scale quickly without just adding more heads.

From your experience, what would you attribute as the best source of conversions on websites?

Word of mouth. Definitely. Those convert at such a higher rate than other sources. I think there is a whole playbook, though to word of mouth and how to inspire and leverage that medium.

What impact did doing videos such as the one that sandwich did for y’all have on your business?

I still love the sandwich video to this day. We did a lot of videos at Slack. Probably one of my favorites is this one:https://www.youtube.com/watch?v=3Vvy872vP3g

For me videos are a way to define your brand and build an emotional connection to it. SEM ads only get you so far.

It also helps as a way to infuse a bit of humor and whimsy.Videos are also often avoided for many companies as they are too hard/complex to put together. So I think you have a bit of an arbitrage opportunity there.

What was your most successful marketing campaign, and what lead to its success?

I’m really proud of the content campaign we put together at Zendesk, where we leveraged top/mid/bottom funnel content we produced and then used them as actual ads to nurture people through the funnel via sophisticated ABM targeting.

In B2B, deal cycles are longer, and from first hearing about your brand to becoming an actual lead, that can be 30 touches and 3 months of time. I think sometimes due to short term pressures, many campaigns just want to skip to the end and get people to sign up via CTA’s like free trial, 20% off, sign up now, but they miss the nurturing aspect.

I subscribe more to the customer eccentricity playbook where you want to have the discovering and buying process be a great experience where the company helps educate you on the market in a fun and helpful way.

_sorry, I could go much more in detail on these answers but I want to try to answer all the questions_

Hey – could you give us an example that was a total game changer when it comes to implementing a specific strategy — meaning all of a sudden, sales just exploded?

A big PR hit will often do that, just give you a massive spike. Same with a really good campaign. But ultimately, I advocate building long term, scalable strategies that get you efficient growth for the long run and help you mint out promoters.

What’s the right time to start with SEO?

Over the last decade, SEO has evolved a lot. I’m not a big fan of trying to out-optimize the system, but rather of creating great content around people’s pain points in your space. That essentially is SEO in my book. Create great content that people love (expressed as links and likes), and you’ll do great in the SERPs.

SEO can be an incredible machine though, and the organic growth you can achieve should be part of any marketing playbook,imho. I’d start very early there.

How did your marketing mix at Slack and/or Zendesk change as the company scaled?

Hopefully it got better

I don’t like playbooks, where you just try to do everything under the sun. You end up peanut buttering everything and then get pretty bland results.

That being said, as the company grows and you prove out your marketing machine (via cac/payback and brand metrics like aided/unaided recall), you can start thinking about leveraging additional $$ to the machine, as you have confidence in those returns.

I want to start a PLG strategy here in my SaaS company. I’m already studying, and I think that I’ll have to deconstruct my Inbound Marketing, Inside Sales and CS Machines and build another entire “machine” using PLG. What do you think I could do to start building this PLG strategy here? What do you think are the first steps we can take or the first things we have to test in order to make it happen? I really think we have a good fit with the PLG strategy by everything I read and I’m seeing in our market.

PLG is really just an extension of the consumerization of the enterprise trend. AKA, make the product easier to use, make the buying experience better, the support experience better, the sales experience better.

That being said, when you are talking about just the “Product” portion of that equation, I would focus in on making it as effortless and easy to try out and use your product as possible. In addition, I would recommend spending time on the visual identity and the editorial tone and voice.

Too many B2B products are bland, sterile, lifeless pieces of dung.

Both Zendesk and Slack leverage simple, easy-to-use interfaces. What are the largest challenges you’ve faced when determining what stays in the product and what needs to be sacrificed?

It’s really, really, really hard to make a simple to use service. I think an incredibly critical eye has to be put on user experience and removing friction from every step.

I love simple, clean designs that bring emotion and guide people through. I often advocated at Slack that we go back and fix bugs before we chase new features. Or even beyond that, go back and make a feature that everyone uses even better (vs. adding a new feature that just a few people will use).

Reactions (adding an emoji to a post), for example, went through so many internal revisions, polish, before we posted it live. The early version sucked. I’m glad we didn’t release it till it was very polished. I’m not a big fan of super agile, get it out and let the users experience it, as often that experience is a buggy, bad one.

Hey! How should a startup CEO brand himself so that it actually benefits the startup itself, and not only the CEO?

You are one and the same for most of the life of the company. Don’t fight it.

Can you tell us a little bit about the strategy behind the “Dear Microsoft” ad in the NY Times? I love(d) it and would be interested to hear what your team was hoping to accomplish and the results you achieved.

Some people loved this, some people did not love it. But it got attention.Sometimes it is necessary to rally the troops.

When to consider an influencer campaign?

Influencer campaigns can sometimes come across as a little slimey. I like giving everyone a great experience and hope they go out and recommend it.

What is your favorite marketing book(s)?

Can I audible with a podcast? I like Manager Tools. That’s not even really marketing specific, but it did help teach me a lot about being an effective manager and leader, and I really like it.

Why has Slack ignored the community platforms? It seems like an easy marketing channel.

Focus has always been on messaging for businesses (not communities). It’s a tough position, because you want to support this, but every cycle/feature you build for communities is not one for your target audience of businesses.

I think Slack was successful, because it resisted the urge to be everything to everyone (like for instance building a pure B2C product), or building marketing automation, or expense management, or the other 10,000 things. I always like the strategy of build a best of breed product and then integrate with the other best of breed products.

Do you have any pointers on standing out in a sea of competition in tech? You seem to have on your resume particularly iconic brands that definitely stand out.

You answered your own question there Evan. Stand out!! A really easy way is to choose a distinctive visual identity and editorial tone of voice. 99% of the B2B companies out there are black and white, bland, acronym filled, lifeless souls. Sorry, that was probably too harsh.

Also when I talk about that, I also mean in the product itself, not just the marketing website.

_btw, I’m so sorry if I missed a question, it’s a little tricky scrolling up and down!_

You mentioned the “right analytics” earlier. What do you think are the most important things to measure in marketing? And what metrics do you use to measure them?

A: – Aided and unaided recall

– Sentiment

– NPS

– CSAT

– Funnel metrics (MQL’s, SQL’S, Pipeline, CAC/Payback).

Lots of good tools out there to track each of these. Build the marketing tech stack!

How would you go about building a brand strategy if Slack had to start over today?

Build a distinctive visual identity, codify an editorial tone and voice, align to a customer centric vision. Think about every single team in the company and the interactions they have with your brand.

In a world where more and more tools allow for automation, what is the best way/moment for marketers to talk and learn from their targets?

Talk to them, listen to them. Events are great for this. I’m also a HUGE fan of NPS. Read and respond to every response.

_I will try to answer every question here. Because you folks took the time out your busy day to ask me a question_

I have three friends who are starting a podcast. Sometimes the content can be rather questionable with swearing and somewhat adult topics. Should they stick to just a podcast or can they use a video platform such as YouTube, also?

I’m a huge podcast fan, and I think as long as you tell the audience upfront that there is going to be some language or sensitive topics, then you are fine. I also like YouTube, just another distribution channel.

In your experience does sales drive marketing or marketing drive sales?

Probably depends on the culture of the company. But I’m a customer centric nut so I’d answer that the customer should be driving both of those teams.

What were the key growth levers you used at Slack to move from a communication tool for eng/product teams to more generalized teams (marketing, operations, HR, etc.)?

An obsessive focus on the overall experience, content marketing, PR, sophisticated ad campaigns, nurturing, IPM, and a bunch of others!

What is your best advice for someone who doesn’t have an Ivy League education to work their way to a C level role?

That it doesn’t matter. Don’t let that get in your head. Luck is the intersection of hard work and grit. Keep grinding.

How do you start with marketing software in a country where no one has heard of it yet, like you did yourself with Slack?

Word of mouth has a way of spreading beyond borders. Also, many companies are international and will adopt tools globally.That being said, paid marketing is usually an intersection point to get into new markets.

Can you talk a bit about your philosophy/approach to trade shows?

Expensive from both time and dollar perspective. They can consume your entire marketing team, so you just have to be careful on the opportunity cost.

In terms of long-term growth, what’s your favorite b2b tactic?

Mint out promoters.

What is the most valuable hard skill in the industry today?

Empathy for users. (_sorry my answers are going to get a little shorter here as I try to get through all these!_).

How did Slack change culture wise once it grew?

We tried very, very, very hard to keep a culture around customer centricity. Our core values were empathy, courtesy and craftsmanship (with a few others), and I’ll always interviewed around those traits.

Which do you think is the best strategy for an early stage’s startup growth: try a lot of strategies vs. focus on a smaller number of things, well executed?

Definitely a small number of things well executed. For instance, if you do podcast advertising, do it better than anyone else. Good luck!

What is the best piece of advice you’ve ever gotten in your career?

Great question! It was this: “Bill, it doesn’t matter if you’re employed or not, it matters if you are employable.” I always took that as I constantly need to be learning and improving.

Do you think a PLG strategy would do a good job in selling to B2B SMBs?

Yes, PLG is just one part of a customer centric strategy, and I think that would work awesome with SMBs.

First mid-AMA coffee break ever on OG. Also, the first cat photo. Treading new ground there.

Wait, that’s not a question. But I made it back to the Flash cat picture. And for that, I salute you, Flash. And you for the nice comment.

Did you know Giphy has always been one of Slack’s most popular integrations? Or maybe it is just me pumping up those stats. Hmmm.

How much involvement do you think marketing should have with customer success and support?

A lot! At Slack, we organized all of the customer facing teams under one leader (me at the time), and I think that allowed us to align these teams together with a goal of delivering a great experience and minting out promoters.

What is your favorite holiday movie?

Christmas vacation!!! Everyone has an uncle Eddie in their family, right?

_Ok I admit no one asked me that question. But it is such a great movie. We should all watch it tonight_

Damn Bill, now they are going to be spamming giphy gif’s in every channel :joy:

Yes, it’s a giphy train!As they should. The question is, why wouldn’t they be putting gifs everywhere. They are little presents waiting to be unwrapped.

How do you determine if your marketing spend was an optimal use of resources?

Pray to the marketing gods. Or good multi-touch attribution software.

What is the most valuable skill and cultural component you have learned while working at Slack and Zendesk?

Be a good person. Customer centricity.

I have an office and team of off shore developers that I want to staff in companies interested in outsourcing. What is the best way to market this in the US, since it seems a lot of companies are not open to outsourcing?

Lots of ways, but I’d find out what vertical you are strongest in and then do an ABM style campaign to that vertical.

How do you perform a marketing campaign for just a target? Not just marketing to a target? Do you send out surveys?

I read this a few times and I’m a little unclear on the question. Sorry about that.

But Target is my daughter’s favorite store. And with that final non-answer, I believe I have reached the end of this wonderful AMA. I hope it was helpful and really enjoyed all the questions.

Thanks for taking the time to chat! Good luck everyone!!