Tell us about your role and journey into technology. How did you arrive at VanillaSoft?

I began my career as a computer programmer and actually coded for over 6 years. At the four-year mark of my career, I started getting bored, staring at my screen all day long. I loved the challenge and the satisfaction that coding brings but I needed variety and distractions. Part of maturing is self-awareness. I recognized then that I needed to transition, but wasn’t sure where to go. Ultimately, I moved from Toronto, Canada, to Stamford, CT, USA, to join a database technology company as a Sales Engineer. It marked the first time my technology background was being utilized outside of programming, and would become a recurring theme in my career.

After several months as a Sales Engineer, the company was pivoting to adapt its product to a new market. I was tasked with helping shape the product for the market’s requirements and suddenly I was a Product Manager. When the product was finally deemed market-ready, I was again tasked with bringing it to the market and suddenly I was a Product Marketer. As fate would have it, my wife and I were having our first child and after much discernment, we decided to return to Canada to raise our family. I joined a startup database company that had been spun out of the University of Waterloo — the MIT of Canada — as their Marketing Manager. That marked the full transition from coding to marketing for me.

After that, it was a series of high-tech companies with ever-increasing responsibilities and budgets and scope. By the age of 29, I was a first-time VP of Marketing at a 40 person re-start in the middle of the dot-com boom. I’ve been fortunate to win many awards in my career, which is always nice to be recognized by your peers. I’ve been involved in numerous acquisitions, sales, mergers, record-breaking venture capital raises, and initial public offerings. I’ve been hired and fired. I’ve been at the top of my career, and I’ve been challenged to reinvent myself. I’ve run marketing globally for the 6^th largest software company in the world, the #1 business intelligence vendor in the world, the market leader in supply chain management, and the biggest provider of public safety software and hardware.

At various times in my career, I was a VP of Sales and Marketing, which gives me very unique insights into the end-to-end revenue generation process — something I highly recommend my colleagues in strictly Sales or Marketing to do. And after years of making money for many people, I decided it was time to run my own company. As a result, I ran a small marketing agency, focused on B2B demand generation and awareness creation, for almost 8 years. And then, one day, a recruiter acquaintance called me and said, “I want you to meet this company called VanillaSoft.”

It was a hard sell. I wasn’t looking to work for somebody again. But, once I met the leadership team, and test drove the product, I knew I had to take the job and close my agency. The market opportunity was too big, the product too good, and the culture too right for me to walk away. That journey began in September 2017 when I became the CMO of VanillaSoft, and it’s hard to believe over 18 months has passed already. They knew when they hired me I was going to push them hard. What was remarkable was that they wanted me to do exactly that. They intentionally hired me to push them hard and to demand more of the organization. That takes real leadership, and that effort was pushed by CEO David Hood. He’s a major reason I took the job. You have to respect the company leader. You have to trust that they are skilled and adept at growing a company and making hard decisions. Neither he nor my fellow colleagues at VanillaSoft, have let me down so far. I haven’t had this much fun in years.

From the time you joined VanillaSoft, how much has the Marketing Technology for Inside Sales and Automation evolved?

The pace of change has been dramatic in the last 18 months. It has been a combination of innovation, new technologies emerging, and existing technologies maturing. The market category of “Sales Engagement” has emphatically emerged, just as “Marketing Automation” did a decade ago, to be a critical component in the revenue technology stack. Inside Sales is a term that has essentially disappeared and been replaced by the term Sales Development. Sales has morphed from a phone or email-based activity to now include SMS, social selling, live chat, and personalized video. Artificial Intelligence is changing the way sales development reps (SDRs) engage with prospects, allowing them to focus on the human-centric tasks, while automating the rinse-and-repeat aspects often associated with email sales nurtures and cadences, and optimizing and personalizing the language of our multi-channel communications to be contextual to each specific recipient.

Sales reps now benefit from near real-time analysis of their live written and verbal conversations with prospects to coach them on when to listen and when to talk, as well as how to recognize buying signals and respond optimally. Buyer intent data gives us real-time signals on potential buyers before prospects have even heard of us and our sales teams can proactively engage with meaningful insights as to what they are seeking. Social proof is a critical element of credibility and as a result customer experience is an integral part of the sales strategy, with a primary objective of driving positive company or product reviews and discussion and awareness.

The line between Sales and Marketing has never been more blurred. Currently, the SDR team reports to the Marketing Head in about one-third of all organizations, a change that would have been unheard of five years ago, and that continues to increase. SDRs now discuss email subject lines, brevity, keyword optimization, open rates, and calls-to-action — all of which were the exclusive domain of marketers until very recently. Both Sales and Marketing share a common vernacular and regularly discuss lead definitions, marketing-qualified leads (MQLs), sales-qualified leads (SQLs), sales-generated leads (SGLs), customer acquisition cost (CAC), customer lifetime value (CLV), monthly recurring revenue (MRR), etc.

Sales processes have never been more templated and A/B testing is now normal in sales campaigns to continually optimize sales engagement. The influences of traditional enterprise applications such as Salesforce.com has lessened as the software options to improve the revenue process has grown from a few hundred apps only a few years ago to well over 1,000 offerings today. The technology stack remains firmly in control of the marketing organization — that hasn’t changed. What has changed, in terms of the stack, is that Marketing, now more than ever, is expected to build an end-to-end platform that meets the needs of both teams while servicing and supporting the Sales organization. However, the one dynamic that remains a constant is the push-and-pull between the two organizations around expectations, accountability, and adoption of the technology stack to meet the needs of the Sales team.

As a Marketing Technology CMO, how would you identify the biggest advantages and challenges of leading a data-driven company?

The biggest advantage is almost blatantly apparent — the more data you have, the better decisions you can make, the sooner you can recognize new opportunities or enhance existing initiatives. Data is the game changer between two otherwise comparable competitors. The challenge with data is more granular; its architecture, integration, and scalability. Marketers constantly try to anticipate the reporting needs of tomorrow based on the knowledge of today, which means they don’t do a great job of it. That results in constant re-engineering of the data schema, never-ending efforts to share information between apps, and thankless hours spent trying to analyze and share the data in a consumer-friendly way that is relevant to each individual stakeholder.

As a result, if a potential technology offering does not have an API or out-of-the-box integration with the rest of the components in your stack, then the likelihood of signing up for that offering drops dramatically. The corresponding with this data challenge is that most marketers are not data scientists, nor do they understand relational database design like computer programmers do. That results in a lot of poor decisions being made that have long-term implications and expensive resolutions. That’s also why the role of marketing or sales operations has emerged to be a critical component in any successful marketing team.

What valuable lessons did you learn from 2018’s massive mergers and acquisitions in the Inside Sales Management industry?

We didn’t learn anything new. This cycle has repeated itself over and over again. The closest parallel is the same M&A activity that occurred in the Marketing Automation category. Every vendor is looking for an opportunity to grow market share while the market rapidly adopts the new tech offerings. That may be a technology acquisition via a small startup, or an install base acquisition of an established provider, or a footprint expansion by a major enterprise solution provider. It’s natural. It also highlighted what we already knew — this market is more than big enough to have at least 5 or more top vendors actively succeeding in each niche. If we learned anything, it’s that we were right in our vision of the market maturing and the push by us to continually expand our customer base, our market awareness, and our influence was the right decision.

Tell us about your go-to strategies to support rapid growth and the lessons learned through periods of massive shift and transition.

Based on my experience, it’s all about being efficient and nimble. If you’re nimble, a small team can react very quickly to new opportunities or new markets before the competition does. If you’re efficient, a small team can do the same work as a large team but in a fraction of the time. To make both of these situations occur, I’ve invested heavily in hiring the right people for our culture, creating repeatable processes that are instantiated in our technology stack so that tech does most of the work rather than the team, and creating a rinse-and-repeat content and campaign calendar that is predictable, repeatable, and scalable. This wasn’t easy. This took a lot of time. It took a lot of money to figure out the right tech stack and how each component should be implemented and utilized. It took discipline to ensure each team member adopted the processes and were accountable to one another.

Finally, it took encouragement and affirmation of each team member, and their individual talents and skills, to create a culture where we all win when we work together with one another, rather than compete and work against one another. When there are massive shifts or transformation, it’s the data that foretells the upcoming shift; it’s the technology that forces the processes required of the new paradigm, and it’s the people who apply their creativity and first-hand experience to figure out what works and what doesn’t before the competition does. Of course, if this sounds easy, it’s not. We still struggle. But we like to believe we are hitting way above our weight class relative to our competitors.

What are the fundamental pillars of running Inside Sales and Engagement practices? To what extent do CRMs and Marketing Automation tools help in achieving the results?

This is a very hard, very open-ended question. I believe the fundamental pillars of running best practices include data, defined sales engagement processes, analytics and shared metrics, non-stop product and market training, sales coaching and mentoring, personal accountability, and mutual respect and collaboration. The tools can manage the data, instantiate the processes in the workflows, provide sales enablement via content sharing and scripting and real-time sales activity recommendations based on machine-learning, automate the engagement cadence across multiple channels such as phone and email and social and SMS, share the reports and provide personalized KPIs, and institutionalize ongoing open communication.

Not all of this exists in CRM or Marketing Automation — between those two items in the stack resides Sales Engagement platforms from vendors such as VanillaSoft as well as Sales Enablement platforms. That is truly where the sales engagement process now happens. Marketing Automation produces an MQL and passes it off to Sales Engagement whereupon they engage and turn that MQL into an SQL. At that point, the SQL is passed off to the CRM where the Account Executive creates a sales opportunity, adds it to the forecast, and tries to close the deal. Tools such as Slack facilitate process-wide ad hoc communication. Everything else in your stack is a niche add-on that bring incremental value to specific tasks or roles. This is the very reason that the Sales Engagement category is now the second most popular inquiry with major analyst firms such as Gartner and Forrester, ahead of Marketing Automation, but still behind CRM, which has morphed into the enterprise backbone across all departments rather than just Sales.

How do you mentor your Product Marketing and B2B Commerce teams at VanillaSoft?

This is a tough one. It’s a never-ending process. We create big, hairy, audacious goals for the team members and the organization. We dream big, push one another, fight, disagree, negotiate, and ultimately, commit to the shared vision. We communicate. A lot. We talk frankly and respectfully hold one another accountable. It’s not always easy, and it’s not for everybody. That’s why hiring for it is such an important aspect of our success. We believe strongly in training and continuing education. We believe in hiring external experts where necessary to ensure the project continues moving forward and doesn’t get hung up on a resource-thin or a knowledge-thin team.

We also believe in empowering and expecting more of our staff than often they expect of themselves. However, these expectations are done in the spirit of encouragement and goal-setting and growth. What we don’t intentionally do is setup any one individual to fail. That benefits nobody. Often, we introduce veteran outsiders to have coffee-dates with our staff and to bounce ideas off of. Sometimes, we hire coaches to work with key members of the team. We value family. VanillaSoft is a very family-friendly company and we intentionally push our staff to prioritize their families over the company.

It’s actually quite selfish because a happy employee at home will be a happy and contributing employee at work. We actively sponsor numerous local networking associations including product management groups, LinkedIn Local, Sales Associations, etc. We push our team members to participate in the community of their craft both locally and nationally. Finally, like all things in life, we pair our staff up with trusted leaders within the organization to be a slightly more mature coach, mentor, and sanity check. It’s all about keeping the lines of communication open, the ideas flowing, and the knowledge shared so that everybody benefits.

What does your technology community look like? Who do you meet at events and conferences to discuss technology?

It’s huge. I have large followings on Twitter and LinkedIn. I interact non-stop with my social colleagues. I belong to several member-only groups where we can candidly discuss our challenges and seek input and solutions in a safe and confidential environment. Obviously, part of that is intentional to create awareness and drive a steady stream of quality candidates to our job openings, but more so it’s about connecting with our/my tribes. I speak often at most of these events.

As I write these responses, I’m attending three conferences over the span of two weeks and will be speaking five times. At events, I tend to meet a variety of individuals, such as:

1. Influencers — We like to learn from one another and create content together to share with our own followers.
2. Marketing leaders — It’s a nonstop parade of “How did you?” and “How should I?” and “Will you help me” questions that we exchange with one another in an effort to succeed at our own jobs and in our respective roles.
3. Sales leaders — Lots of discussion around sales processes, technology stack choices, tactics to drive more leads, etc.
4. Industry analysts — Many coffees occur discussing the future and the trends and what I’m seeing and what they’re seeing.
5. Sales reps — The selling never ends and sales reps want me to buy their wares because I have budget and authority.
6. Customers — Our customers love us, and they consume all of the content we create so often they want to talk product and they want to meet me face-to-face rather than just as an individual in their timeline.
7. Prospects — Like customers they’ve read and watched and listened to the content that I produce and they have more questions about what they should do, will our product fit their needs, how did we solve certain problems, etc.
8. Partners —We are constantly being sought out to work together on a joint offering, OEM deal, product bundles, etc, so these discussions are often technical-focused or market-opportunity-focused to ensure alignment or not.

What are your predictions on the most impactful disruptions in Marketing and Sales Technology for 2019-2020?

Sales Engagement continues to dramatically change every sales organization and every standard tech stack. It just fixes so much of what has historically been inefficient in sales. That’s the biggest. Artificial Intelligence will continue to grow, however, I suspect the hype may exceed the reality in the near-term. Video and its adoption will be massive across social selling, live meetings, marketing email nurtures, sales cadences, and awareness creation and influence development. LinkedIn and its growth and adoption will continue to rapidly expand, like Facebook in its early days, as a channel to identify and source new leads. Buyer intent is rapidly emerging as a huge next wave of investment; buyers are getting sales involved lower and lower in the funnel and buyer intent allows sales to get involved much sooner in the funnel and pre-empt the competition.

What startups in the technology industry are you watching keenly right now?

Ohhh…. That’s a tough one. I don’t want to give away any secrets. Obviously VanillaSoft. LeadSift is another. Everstring is intriguing. Drift is pushing the boundaries of live chat and its applications. Accompany was just acquired by Webex (Citrix) and they were very interesting.

How do you prepare for an AI-centric world as a B2B marketing leader?

I’m cynical. I want to see the proof and I choose not to believe the hype. For AI to truly work, it requires massive amounts of data. Most organizations do not have that. Hence, if you extrapolate the data to the industry and not just one company in that industry, the findings and recommendations that AI will generate may be true but irrelevant to many individual companies. I believe we’re solely at the stage of Machine Learning for the most part. If we accept that, Machine Learning has the ability to eliminate the repetitive, non-value-add aspects of our processes so that we can focus on the value-add aspects of what we do. This is fantastic news.

Does this mean the death of the SDR because AI-based bots will have conversations between buyers and sellers, thereby cutting out the human aspect and making us redundant? I believe we’re a long way from that. I do not see a singularity anytime soon on the horizon. However, those same AI-centric bots give us marketers some amazing tools to better engage, analyze, and understand our buyers so that we can create even more complementary campaigns to win more business. That excites me.

How do you inspire your people to work with technology?

I position technology as a competitive edge. As a vendor who may not be as well-funded, or have a smaller team, technology gives us tools to use to level the playing field. If we’re aggressive and utilize it in ways nobody else is doing, we beat our competition every time. It’s all about pride. It’s also about building a compelling resume. It’s also about having a chance to do cool stuff that other employers might not let them do. In the end, I don’t really need to inspire my team to work with technology. They want to. They love their jobs and they like to beat the competition.

One word that best describes how you work.

Frantically.

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

• iPhone
• iPad
• DJI Osmo Pocket video camera
• Logitech Brio webcam
• Rode Podcaster microphone
• Apple Airpods and/or Bose QC I headphones
• Slack
• LinkedIn
• ZoomInfo
• DivvyHQ
• Adobe Creative Suite (Premier, Audition, Photoshop)
• SEMRush
• BuzzSumo
• Grammarly
• Zubtitle
• CloudApp

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

Magnet (app for my MacBook ensures all of my screen real estate is optimally organized when I have numerous apps open) — eliminate the Alt-Tab syndrome.

What are you currently reading? (What do you read, and how do you consume information?

• Clive Cussler – “Shadow Tryants“ (Fiction)
• Trish Bertuzzi — “The Sales Development Handbook” (Non Fiction)
• I am a voracious reader. LinkedIn and Reddit are a nonstop part of my daily routine. I’m also a news junkie and have multiple news apps on my phone.
• I read fiction to shut off and tune out. I do not do this nearly enough.
• I read a lot of sales and marketing research to continually optimize my approach to the market and to campaigns. If I can learn a trick that improves my results by even a few percentage points then I want to know what that trick is.
• The least consumed on my list would be sales, marketing and management books. I value a handful from those whom I respect but otherwise would rather talk to an individual directly and learn from them rather than read about it.

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

It’s better to do it and ask for forgiveness then never do it at all.

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

I am told that my energy is infectious. It comes across in video and audio. It inspires my staff to achieve more than they thought they could. It opens opportunities up to connect with people who might otherwise never even know I exist.

Tag the one person (or more) in the industry whose answers to these questions you would love to read:

Benjamin Dennehy – The UK’s Most Hated Sales Trainer.

Thank you, Darryl! Hope to see you back on MarTech Series soon.