Arthur Castillo

Senior Manager of Field Marketing & Community at Chili Piper

18 Insights · 6 Questions · 12min Read · 15min Listen · Connect with Arthur on LinkedIn

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Turn champions into raving fans. High leverage principles. A sales rep that broke into marketing. Bypass the SDR qualification. 83% show rates on first inbound meetings. Keep your brain activity as fresh as possible. Scaling the team and delegating. Ask about “where they're trying to get to.”

Here’s what Carl Ferreira said about Arthur:

Arthur Castillo. Over at Chili Piper. They're a great team. We're a customer. Arthur is a dear friend and he just has such a unique perspective. He actually comes from sales and now is in marketing. So he's a fantastic resource. He really understands the entire revenue org, the entire customer journey, and is a big, big resource there for thinking innovatively about how those two teams can work together. —Carl Ferreira, Director of Sales at Refine Labs → listen

What are 3 ways your team converts your market into revenue?

1) Inbound, for sure. Our marketing is responsible for driving over 60% of our pipeline, or more than that, and part of how we do that is we get our highest intent leads to book a meeting right there. So, instead of focusing on the classic “speed-to-lead, let’s get in touch with them in under five minutes,” although I think that's important, I don't think a lot of people are thinking about “speed to meeting booked,” or “speed to first meeting booked,” and we make that happen within minutes. So it really helps capture a lot of those high intent buyers, and for those of you that may or may not know, in B2B tech, less than 40% of those demo requests make it to the first meeting. So, you're leaking out 50-60% inbound pipeline, and we, last I checked, had an 83% show rate to first meeting, so pretty high there.

2) Next, our outbound model. So, I think our SDRs do an incredible job at multichannel, specifically mostly on email and LinkedIn. We get praise every day from the outreach that they send, as well as some people people try and poach our SDRs. So that’s a good sign there. The difference in what they do there: it's not necessarily as personalized as maybe some people think, but it's very contextual to how they do their job, and highlighting, “Hey, are you going through these changes? If, so this is how a customer in your space solved it.” So very contextual to the specific person they're targeting.

3) And then lastly, we turn Chili Piper champions into raving fans. So we're highly active and engaged on our social networks, specifically LinkedIn. We're always trying to give shoutouts to champions. One of the things that I thought was really cool: we did a thought leader series recently on marketing leaders. The prize for that was a trip for two to anywhere in the world. They obviously enjoy that, and we've used a lot of these distribution network effects of our Chili champions. We've noticed that when these referrals come through, they're closing at the highest rates, much higher than inbound or outbound.

So I'd say those three are inbound motion, our outbound motion, as well as turning Chili champions into raving fans.

What are 3 hard problems you recently overcame?

1) I am a sales rep that broke into marketing. It kind of happened by chance, but what I've noticed is that since I've been a little bit more vocal about this, I've actually had quite a few sales reps reach out to me and say, “Hey, your article really resonated with me about breaking into marketing. I'm trying to find my footing here in sales, but I think maybe I'm a creative and I'm better equipped to be in marketing.” So that's been pretty cool. And I've been trying to share a lot of how I've done that. I've wrote an article on my LinkedIn, so feel free to check it out to any of those creative sales reps looking to potentially break into marketing

2) Sticking with that theme, I will say project management is an ongoing problem that I'm trying to overcome. I didn't really have to manage a lot of projects as a sales rep, and now coming into marketing, you have to look at content marketing or product marketing, marketing operations, all of these different things to make sure that you're able to get things through. So that's been a change, but I also noticed that this was part of my skill set that maybe I was a little too afraid of, or didn't see a fit for it, and now that I'm doing it, I can see how it would actually be super useful for really anybody, sales reps, marketers, anybody, to better understand your project management.

3) Saying “no” to people. I'm still pretty guilty of not doing this, but I've noticed as I'm becoming maybe more of a public figure here at Chili Piper, I try and think of myself as a brand advocate, a lot of people would approach me before in terms of trying to apply for a role or maybe trying to pick my brain about something. As much as I want to do that, I am getting more and more responsibilities, and if I say yes to something that means I'm saying no to something else. I really have to push back a little bit. One tip I have for that, something I've been doing, is saying, “Hey, I can't do it right now. I get quite a few of these calls every week, or these asks every week, but let me know maybe what's top of mind or what position you’re interested in. I’ll create a five minute video trying to answer their calls and send it to them. It’s much more effective than hopping on a call with them, spending 20-40 discussing things that are top of mind fo them.

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What are 3 roadblocks you are working on now?

1) Attribution model. We are last-touch attribution, but we are starting to shift that, and that was a little bit of a roadblock for us here in the Field Marketing and Community because it's not as direct response as maybe Demand Gen or Outbound Sales. So, just because they attended an event doesn't necessarily mean they're ready-to-go right after it. And, because we’re last touch attribution, a lot of what I’m comp’d off is kind of those qualified held meetings coming through events. So we are starting to change that more to an engagement model, and getting all revenue departments going after engaged accounts, I'm really looking forward to that.

2) Scaling the team and delegating. Coming into marketing, I'm actually a first time manager. So, I’d put scaling the team and delegating. I think being a new manager, I recognize where my strengths are, and sometimes I want to hold on to certain things, but at the same time, having those priorities, I do have to delegate certain things that maybe in the past I would have wanted to do. And with that, understanding how I want to scale my team here at Chili Piper from a Field Marketing side.

3) It’s funny, what probably got me into marketing was my LinkedIn presence, and I hadn't been putting as much time into that. So I'm trying to find a balance between executing on my job and my responsibilities while still staying top of mind and having that LinkedIn presence. That’s been a little bit of a roadblock.

What are 3 mental models you use to do your best work?

1) High leverage principles. I don't know if this is how it's labeled, but I was taught this by my manager, Dan, as I moved into Marketing. So in trying to explain it, a high leverage activity is maybe something that you create once, a system or a process, and that you can reuse it. So we're not starting from scratch. Whereas a low leverage activity will be, I'm doing it once, so I'm having to recreate it from scratch. I'm really not building any systems or processes. So it's helped me understand, “how do I create this so I'm going to be scalable? How do I do things maybe once or twice and it serves me for a longer amount of time?”

2) Touch it once. And this is for focus. Get your mind out of the gutter to all your listeners. I heard this from a book called Getting Things Done as well as other productivity books. And the concept is if you are getting ready to, let's say, tackle a task, make sure that you have the time ready for that. Email is a huge one. If I'm going to open my email, it's not to scroll through and see what messages I have. It's either to maybe delegate, maybe defer to later time, and say, “okay, this one's going to take a longer time. And if it's less than two minutes and I can respond right then and there, that's only when I'm opening emails.” So I'm not constantly being bombarded, making sure that if I'm opening up any of these tasks, I stay focused and I touch it once.

3) Keep my brain activity as fresh as possible. I don't know if this is necessarily a mental model. I try and stay, how do I say, I keep my brain activity as fresh as possible. Even if for the trained professional, you can only stay focused 90 minutes at a time. So, instead, what I try and do is find times in my day to do activities that I know bring energy back into my life. Whether that's taking a quick walk outside, getting some fresh air. I found meditating super helpful. A quick 10 minute meditation in the afternoon, in particular, has really helped me get that extra boost. I have been trying to get off the coffee. So I think, in terms of productivity, how do I look at my day and have these built-in breaks that I know give me energy versus drain energy?

What are 3 techniques that GTM teams need to try?

1) Direct mail, but with the QR code attached. The first one that came to mind for this, and something we've been really experimented with recently is direct mail, but with the QR code attached. So I think direct mail is great. There's a lot of awesome vendors out there, but In terms of buyer journey, always thinking about, “how do we remove friction and make it easy for them to engage?” I think this QR code is really going to be this point of conversion where, “wow, thanks for sending me something. If I scan this here, it's an easy, direct path. For us, we either send them a quick video with a link to our Chili Piper booking links or a direct link saying, “Hey, we'd love to discuss a little bit more.” So that's been something really cool. We've already seen 80%+ engagement for anything we send out with a QR code, and much higher click-through rate than anything we've done in LinkedIn or emails. I definitely encourage people to look at that.

2) Bypass the SDR qualification. I think we are still looking at buyers probably where they were 10-20 years ago. Now they're much more educated than they ever were. They have access to peers, communities, LinkedIn where I can message you directly and say, “Hey, how are you solving this challenge?” Yet, we're still treating them as if they're starting from scratch. So we need to meet them where they are at in their journey. And oftentimes, it's this SDR qualification call with people trying to prioritize speed-to-lead that actually hurts the customer journey. And they say, “Seriously, you're going to ask me questions like, if I have budget, authority, timeline, when I’m so much further down the funnel?” It actually harms your inbound process. Once you have a good understanding of your ICP firmographics, title, there's ways in which you can bypass that SDR qualification, get it routed straight to an AE, and we've seen win rates increase up to 3x doing that. Maybe for the edge cases, you can still route them to an SDR to help them understand, but I think bypassing that SDR qualification is huge.

3) Ask about “where they're trying to get to.” This is a tough one, because I think when it comes to qualification, we always talk about “where they're at today,” but we never ask about “where they're trying to get to.” I can't tell you how many times where even SDRs that are referring to me have they said, “the qualification doesn't really meet what we're looking for, but it sounds like they're pretty interested in setting up a call. Are you interested?” Sure, I'll take the call. And then, two weeks later, I figure out their reason, they’re raising Series A. So they're not qualified now, but two weeks later, they are? Silly process. Let's talk to them about where they're trying to get to. Another thing on that: sometimes we are too obsessed with our ICP. I heard Craig Handy talk about this where he looked at the ICP qualifications for previous years Closed Won revenue for a client of his. He found that 60% of the Closed Won revenue technically would have been disqualified because it didn't meet their ICP qualifications. So a lot of the time, again, let's ask about where they're trying to get to? Or, maybe what they tried to do prior to reaching out to us, because often it could just be a simple switch or a tiny little product feature now that can expand an entire new industry and TAM for us, yet we’re disqualifying them. So, let's talk to those people, understand not necessarily where they're at today, but where they’re trying to get to.

Who are 3 operators that should be our next guests and why?

1) Alexine Mudawar. She's one of the most talented sales reps I've had the pleasure of knowing. I'm pretty sure she gets 300% quota every year, and that’s partly due to her writing a 50-page business plan every year on how she's going to hit her metrics and back until her goal.

2) Jacob Gebrewold. From Klue. He's new to the software SaaS space, and he's absolutely crushing it as an AE. I think he's a very unique content creator and he understands how to stand up from crowd, but also have buying conversations that engage his prospects, which by the way, are Product Marketers, and he's never been a Product Marketer. I think he's really changing the game from that perspective.

3) Jed Mahrle. Last but definitely not least. I truly believe this guy's going to be a CRO. He's changing the way people approach business development. He runs global business development for PandaDoc and some of his tips I’ve read, I've never seen anywhere else. I think he's really a practitioner. So he's not just talking about things from his mind, he's executing in the field and then sharing what's working.

Work with Arthur → Chili Piper is hiring!

March 2022 · Interview by Chris Morgan, Host of Market-to-Revenue

Market-to-Revenue Podcast ⚡️ Lightning-fast interviews with GTM operators in sales, success, product, and marketing.

🔊 You need to meet:

Shea Cole

VP Marketing at Fullscript

Anita Toth

Chief Churn Crusher

Darren Sharpe

Chief Revenue Officer at SuiteSpot

Anthony Murphy

Founder of Product Pathways

Craig Handy

Head of Revenue Automation, Tooling & Enablement at Shopify + Founder of Jameson Strategies

Mo McKibbin

Head of Customer Support and Success at Moxion

Vladimir Blagojević

Co-Founder of fullfunnel.io

Jason Bay

Chief Prospecting Officer at Blissful Prospecting

Katy McFee

Founder and Principal of Insights to Action

George Valdes

Head of Marketing at Monograph

Matt Baxter

Director of Product Management at Bestow

Kristi Faltorusso

Chief Customer Officer at ClientSuccess

Daniel Cmejla

Director of Partnerships, Community & Social Media at Chili Piper

Shri Apte

VP Revenue at Triplebyte

Dani Woolf

Director of Demand Generation at Cybersixgill

Antoine Buteau

Business Operations at Replit

Brandon Fluharty

Founder of Be Focused. Live Great.

Meghann Misiak

Founder of The Path to President’s Club

Ryan Paul Gibson

Founder of Content Lift

Jacob Gebrewold

Commercial Account Executive at Klue

Sidney Waterfall

VP of Demand Generation at Refine Labs

Sam Kuehnle

VP of Demand Generation at Refine Labs

Andrew Miller

Senior Growth Product Manager at Monograph

Darren McKee

Director of Growth at Wellthy

Sean MacPherson

VP of Customer Success & Experience at Alyce

MJ Peters

VP of Marketing at CoLab Software

Patrick Coleman

VP of Growth at Replit

Arthur Castillo

Senior Manager of Field Marketing & Community at Chili Piper

Leslie Venetz

Founder of Sales Team Builder

Stuart Balcombe

Product Marketer at Arrows

Jen Allen

Chief Evangelist at Challenger

Carl Ferreira

Director of Sales at Refine Labs

Mark Znutas

Vice President of GTM Strategy and Operations at Hubspot

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