Tell us about your role at Outreach and how you got here. What’s the most fascinating aspect of leading a Sales Engagement software platform?

I’m the CEO and co-founder of Outreach. My job is to make our customers successful by hiring the best talent around and uniting them to further our mission. Some days, that means diving into strategy with my product team; other days, it means digging into the pipeline with my sales leaders. I’m dedicated to all aspects of Outreach’s success.

Before founding Outreach, I was employee number three on Amazon’s AWS team and later moved to Microsoft to lead their mobile division, taking that from launch to $50M in annual revenue. At the core, I’m an entrepreneur and have always been interested in building my own business. That’s what led me to enroll in Techstars’ 2011 class, along with my three business partners. We founded a company that was essentially a marketplace to connect teams of developers to the companies looking to hire them. But we were struggling to handle the volume of prospecting required to build both sides of that marketplace, so we built our own platform to help our sales team of one operate like a team of 10. The companies we sold to were much more interested in buying that platform than our recruiting service, so we eventually doubled down on building that out. That was the genesis of what has become Outreach.

The most exciting aspect of leading Outreach is pioneering a brand new category: the Customer Engagement Platform. For far too long, field teams have been shackled by technology like CRM that demands more than it delivers. There’s tremendous pressure on Sales, Marketing and Customer Success leaders to drive revenue growth while delivering a flawless customer experience. They need and deserve tools that help them work smarter, more efficiently and more collaboratively so they can meet both goals. That’s why our company and category are growing so rapidly — we address a massive pain that is felt by almost every B2B company.

Given the changing dynamic of marketing and sales technology landscape, where do you see Outreach fitting in a CMO’s stack?

The last 10 years have seen massive shifts in marketing technology, allowing Marketers to operate like scientists, tuning the dials to adapt to every learning and insight. But in that decade, little has changed for Sales — they’re still using CRM, essentially a database in the cloud that does nothing to help them execute selling.

Outreach takes a completely fresh approach to the old ‘sales as usual’ mentality, freeing up sales reps and giving them back valuable time in their day to focus on selling. Sitting atop the traditional CRM, Outreach’s automation and machine learning capabilities, paired with our analytic and reporting tools, make for a key component of any CMO’s stack by streamlining the sales process and increasing sales success.

What is the ‘State of Sales Engagement Automation’ technology in 2018?

Sales engagement has continued to become more defined and acts as an essential aspect of selling in 2018. With Salesforce announcing their plans to enter the space, it’s evident that this category is growing since we established it with Forrester in 2017. Looking to the future of sales engagement technology, Outreach remains dedicated to enhancing and building upon our platform with the latest in AI and machine learning.

What were the key takeaways from Outreach’s Unleash? How do B2B events enable customers to make better decisions in improving their tech stacks?

Unleash is unlike any other conference — it was created as a way to make lasting connections with the leaders and innovators shaping the next era of selling.

This year, Unleash sold out. It drew over 650 sales leaders who had the opportunity to learn from those at the top of their game in fields as diverse as psychology, health and wellness, and the military. We kicked each day off with a group workout varying between yoga and navy seal training, hosted breakout sessions ranging from leadership talk tracks, to deep dives into machine learning and analytics, to mission planning on how the military planning model applies to business, and we ended with a Top Gun-themed party at the museum of flight. We ensure each year’s event is fresh, inspiring, and full of unconventional surprises — a lot like Outreach itself.

Overall, B2B events provide a great opportunity to gather industry members together to network, learn from one another, and understand their respective landscape on a deeper level.

What does your ‘Ideal Customer’ Profile look like? Which industries are best suited to benefit from Outreach’s Sales Optimization and Productivity Suite? Which new geographies are you currently targeting?

Outreach is designed for B2B companies of all sizes — from Fortune 500 to high-growth startups — and for every customer-facing role. Prospecting reps use Outreach to generate more pipeline through orchestration and automation of the entire prospecting workflow. Account executives use Outreach to close more deals with automated meeting follow-up and rescheduling. Account managers use Outreach to drive renewals and upsells with workflows that automatically kick off based on signals (i.e. new seats are added to account).

While Outreach is mainly focused in the US currently, we do have global customers in the UK and Germany.

How do you leverage AI/ML and Data Science at Outreach to scale your marketing efforts?  What are your predictions on the most influential disruptions in B2B Marketing powered by AI/Machine Learning?

Outreach utilizes AI, machine learning and data science throughout its platform. Most recently we enhanced these features with Outreach Amplify, a new program that uses machine learning to scientifically measure, test, and optimize the performance of sales teams while automating non-selling tasks on their behalf. We also introduced Outreach Meetings earlier this year, an automated scheduling tool that accelerates and simplifies the scheduling workflow with prospects.

I predict integrations that provide actionable insights that humans can trust and act upon will be the most influential disruptors in AI/machine learning moving forward. Ultimately, technology innovations aren’t about replacing human analysis and decision making — the focus should be on amplifying it.

What marketing and sales automation tools and technologies do you currently use?

At Outreach, we eat our own dog food. The platform was originally developed for internal use when my co-founders and I were focused on our first startup GroupTalent, a recruiting company. With three months of cash in the bank, we scrambled and built a workflow that would allow us to sell faster, allowing our team of only three people to sell like 10. That workflow was the early stages of Outreach, and we still use it internally today and credit a large aspect of Outreach’s own rapid growth to the effectiveness of the platform.

Could you tell us about an outstanding digital campaign at Outreach? 

We have strong relationships with all of our customers, and their testimonials say it all. But one of our earliest customers still has one of the most memorable case studies for me, and that’s Cloudera, a global data management provider.

In Cloudera’s sales team, each rep was doing things differently — despite the company’s investment in training best practices — because it’s hard to enforce and ensure processes are being followed. Since implementing Outreach, the sales team has had access to the tools they need to be extremely productive with a minimal amount of training. The sales team confirms that Outreach is not only a time saver; it has increased their average email open rates sixfold, with 30-60 percent of emails being opened. Reply rates also increased from an average of three to 20-30 percent. What’s more, the number of meetings Cloudera’s sales team was able to set more than doubled, marking a record number in their target market within five months of implementing Outreach.

How do you prepare for an AI-centric world as a SaaS business leader?

The old saying, ‘If you can’t beat them, join them,’ comes to mind. We know the effect that AI is having on the SaaS ecosystem. To prepare, you must stay ahead of the curve, invest in it, deploy it, and continue innovating upon it.

At Outreach, we’re currently heavily focused on building out our AI/machine learning arm. Earlier this year, we brought on Pavel Dmitriev, former principal data scientist, analysis and experimentation at Microsoft, to head up our machine learning team. He has played a pivotal role in helping us continue to broaden our data science expertise and launch our machine learning tool for sales: Outreach Amplify.

How do you inspire your people to work with technology?

At Outreach, we take culture seriously — it’s absolutely critical to our success. We embody grit, passion and drive. We inspire each other every day to do our very best.

Because we greatly value these traits, it’s my mission to ensure that Outreach’s employees and customers are successful with our technology. For Outreach, this means understanding people’s inherit passion and knowledge for technology and pairing it with the most intuitive onboarding processes.

One word that best describes how you work.

Learn quickly!

What apps/software/tools can’t you live without?

Ommwriter, Asana, Gmail, the phone, and my notebook. I can live without much of these, except the phone and the notebook.

What’s your smartest work related shortcut or productivity hack?

Voice memo dictations for my virtual assistant to transcribe.

What are you currently reading? 

Book of Why: The New Science of Cause and Effect

What’s the best advice you’ve ever received?

Be tactically impatient and strategically patient.

Something you do better than others – the secret of your success?

Empathy: I can only be genuinely interested in people; I have a bottomless curiosity to understand people.

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