SalesTech Star

SalesTechStar Interview with Darryl Praill, Chief Revenue Officer at VanillaSoft

Tech marketing expert Darryl Praill recently moved from the role of CMO to CRO at VanillaSoft; he joins us in this SalesTechStar interview to talk about this exciting shift while sharing a few revenue tips and fundamentals that can help B2B marketing and sales teams tide through the challenges bound to the Covid-19 pandemic.


Tell us a little about yourself, Darryl? Moving from CMO to CRO is exciting, what are some of the plans you have in mind for the near-future at VanillaSoft?

I’m Darryl, I’m 52 years old and have been blessed with a wonderful wife of over 30 years. My 25 year old son is a morning news anchor for Global Television in Regina, Saskatchewan, Canada, and my 24 year old daughter is a customer support champion here at VanillaSoft!

After college I had my first stint in sales as a door-to-door photocopier salesman, but quickly realized that was hard and subsequently decided my degree in computer science might be a better career path for me. After several years of doing that, the sales and marketing passion began to assert itself. I left coding to become a sales engineer. That position led me to eventually become a product manager and then a product marketing manager. I ultimately became a full-cycle marketer for a small database technology company. Two acquisitions later, within about six months, and I was suddenly running marketing globally for the sixth largest software company in the world. By 29 years of age I became a first-time VP of Marketing. Later stints had me as either a VP of Marketing or a VP of Sales and Marketing at numerous high tech firms. Along the way I’ve raised almost $100 million in venture funding, bought and sold companies, gone public multiple times, and been fired. Some more notable accolades have me as a 2020 Top 10 SaaS Branding Expert, Top 19 B2B Marketer to Follow, Sales World Top 50 Keynote Speaker, award-winning podcaster and a recognized social media influencer. I joined VanillaSoft in late-2017 as their CMO with a sole task of filling the sales pipeline and generating world-class awareness and thought leadership.

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Recently, I was appointed as VanillaSoft’s first-ever Chief Revenue Officer. It’s a daunting role at an industry-leading software vendor that is a recognized top vendor for one of the hottest software categories in the B2B world – Sales Engagement. With a solid, yet predictable, 30-60-90 day plan of Assess-Revamp-Deploy my days have been consumed with understanding the people, the processes, the technologies, the strengths, the weaknesses, and the opportunities of my organization. As a result, we are actively transitioning the team from a historically inbound-lead revenue machine to an outbound-centric, Account-Based Marketing (ABM) driven, strategic selling organization. That means a completely new way of selling, with new supporting technologies and processes. We are transitioning to a highly-targeted, consultative, challenger sale rather than simply taking orders and processing credit cards. While this is a dramatic shift in culture and execution, it’s an absolutely amazing time to work here and experience the transition and be part of a once-in-a-lifetime masterclass. My days are long, my sleep is minimal, and I’m having an absolute blast doing it. What makes it all so satisfying is that I’m surrounded by colleagues, and internal leaders, of such incredible integrity and character that I feel both encouraged and supported as we tackle this journey together.

The ongoing Covid-19 challenges have forced teams to realign and restructure how they work while being remote: besides redefining work processes and methodologies, as a revenue leader now, what are the changes you are focusing on the overall processes to help drive revenue goals? 

As part of our ongoing response to COVID-19 challenges, we’ve implemented a few specific changes:

  • We’ve identified the existing industries we target where there has been a dramatic impact (i.e. hospitality, travel, tourism) and have worked to assist them as much as possible to ensure their viability. For many, this simply means pausing existing contracts with no penalties.
  • We’ve pivoted to new industries that have dramatically expanded, or emerged from nowhere, and quickly shifted to pursue them and assist them with the increased demand they’re suddenly experiencing. This was a rapid-fire effort by our marketing team to create content, messaging, and awareness, as well as forcing our sales team to rapidly get up to speed on new markets and prospects.
  • We’ve implemented a complete ABM sales and marketing strategy including defined target lists of large accounts, named accounts, and industry accounts for each vertical-specific sales-rep. We augmented that with new ABM technology from Terminus and a new CRM platform for our account executives to provide them with the massive intelligence and insights necessary to engage with prospects.
  • We’ve created two entirely new teams:
    • Revenue Operations to manage our emerging stack and constantly evaluate the data to know what works, what doesn’t, and where there is unrealized opportunity.
    • Sales Enablement to train, coach, and support our sales reps and equip them with the tools necessary to succeed in sales.
  • We’ve hired additional sales staff who are experts in our newly targeted markets.
  • We’ve hired multiple sales engineers to help our account executives deliver amazing proof of concept for our larger prospects. This is a brand new role and reflects the needs of ever-more-complex sales technology environments.
  • We’ve hired external sales trainers to ensure our reps have the skills necessary to be best-in-class sales professionals.
  • We’ve implemented ongoing product training so that our reps have the right answers and knowledge to support the varying requirements of so many different industry verticals we now pursue.
  • We’ve committed to ongoing training by implementing “book club” concepts around industry sales thought leaders and their content.
  • We’ve recommitted to ongoing communication and sharing, using tools like Slack and Zoom, to ensure all work-from-home staff feel connected.

What according to you should revenue teams and sales, marketing teams, in general, be doing more of during this time to try and end the fiscal year with good results, given the last quarter has been a tough phase for most?

Hyper-focus. Go deep and make a compelling case for your offering in significantly smaller, more defined market segments. It’s tough to compete with all of the noise generated by all of the vendors and service providers across a general or horizontal market. However, if you can be the absolutely best vendor in a small, defined market then business will come to you via word-of-mouth and personal referrals.

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Add value. More than ever, prospects are looking for help, insights, guidance, and best practices. Stop pitching about your product or services. Nobody cares. Instead, create amazing content that details everything a prospect needs to succeed with zero expectation that they will engage you. Ultimately, everybody wants help to ensure they succeed. The question comes down to whom they trust the most to assist them and help them achieve their goals. More and more, that choice is based on whom they most respect within their industry. That should be you. Your content will create that trust and respect level to earn their business.

During this pandemic, what were some of the biggest challenges/lags you’ve noticed in tech marketing and sales teams? Closer home, at VanillaSoft, what were some of the things the company had to struggle within the initial phases of the Covid-19 outbreak?

There were several mistakes made as we managed this transition. With nothing to compare to in modern times, most were unprepared to make the changes necessary. Some examples include:

  • Changing playbook messaging for phone, email, and social media. The old email and LinkedIn templates were deemed tone-deaf, irrelevant, or insensitive when there was so much uncertainty, so much fear, and so much anxiety. Many vendors were perceived very poorly as a result.
  • Changing targets and expectations. Too many sales leaders assumed their teams could still hit their targets (dials, conversations, demos, etc.). Even when it became apparent that wasn’t going to happen, many just doubled-down by increasing their activities. The issue was never about activity, but simply about people holding their breath and pausing their spend to assess what was going to happen and how they needed to respond to survive.
  • Mistaken beliefs that they could simply start backfilling their top-of-funnel lead creation by having webinars or virtual events with no actual value-added content. They were too busy focusing on pitching rather than sharing advice and insights to help their target markets navigate the turbulent waters.

At VanillaSoft, we had our own challenges:

  • A lack of information initially made decision making difficult. Do we do nothing and wait? Should we be identifying staff to layoff? What if our prospects cancel their contracts en mass? Do we have sufficient cash flow and financial reserves? There was a lot of scenario playing taking place so that we had a plan ready, but that can sometimes lead a firm to suffer paralysis by analysis.
  • Connection rates dropped for outbound phone activity. That has historically been our biggest strength. Accordingly, we had to adapt and adjust to move more to social media, partnering with complementary partners to share leads, and to source additional contact methods such as mobile phone numbers.
  • Knowing when it was time to pivot and identify new markets that could backfill our reduced sales activity and lead flow. This greatly stressed the organization as marketing needed to very quickly develop messaging and value props and content to be credible in these new markets, and sales needed to become overnight experts so that they could have relevant conversations with prospects. This was potentially the biggest stress-inducer for us.
  • Customer Support was overwhelmed as many of our existing markets (i.e Insurance, Healthcare) surged during this crisis with people requiring more of their services, so those clients needed to rapidly expand their VanillaSoft licenses.
  • Managing the increased burden of our clients suddenly moving all of their sales representatives to work-from-home and those reps now requiring VoIP-based softphones. Our Support team was stretched to keep up with the demand to fulfill these historic spikes in demand.

For companies who are still fine-tuning their strategies to help drive business for the rest of the year: what are the top revenue generation tricks, you would share with them?

Inbound marketing is only getting bigger and more effective. Killer content with in-depth guidance and advice is being consumed at record-setting levels. That can become a very effective lead generation vehicle.

Virtual events have replaced the legacy trade shows and regional summits. People still want to network and learn from others with one-on-one lessons. Organizing a series of virtual events or partnering with others can generate the visibility and the lead flow you need to identify prospects who are in-market for solutions.

Influencer-marketing is, more and more, an amazing vehicle to associate your brand with market thought leaders, and to benefit from those influencers driving prospects to you. In many ways, this is another form of referral, or word-of-mouth, and we all know those leads historically convert the highest.

While remote work is still largely in place due to the ongoing Covid-19 pandemic even though businesses and economies are slowly inching towards reopening, what are some of the thoughts you’d like to share for teams, businesses, marketing and sales teams in general – best practices they should follow in this new normal?

There are a number of considerations that are easily overlooked yet so effective at ensuring your team’s cohesiveness and effectiveness:

  • Constantly communicate. You cannot over-communicate, but you can absolutely under-communicate –  to your detriment. Have company-wide updates. Have virtual lunches. Have team virtual social gatherings. People need to continue to see, and engage, with one another regarding both work and non-work activities.
  • Slack or Microsoft Teams is essential. Push the organization to not cocoon or hide behind email. Get them actively communicating one-on-one or in topic/team-specific channels. When the sales team all works-from-home, there is nobody there to hear a gong ring when a new sale is booked. There is nobody there to ask how you should have approached a prospect, or to get feedback on an opening line you used. Slack or Teams can offset many of these shortcomings. Employees want to feel like they’re part of a tribe, rather than lost on a deserted WFH island.
  • Make your messaging relevant. We are not living in normal times. People are scared. They’re anxious. They’re stressed. They’re worried they might lose their job. The last thing you can do is use messaging that assumes none of this is taking place, or doesn’t even acknowledge their hardship. Update all of those templates to reflect the modern selling era and requirements.
  • Talk to every single one of your employees, one-on-one. Even with team channels on Slack or Teams, many employees will not share their personal concerns, or challenges. Left unresolved they will only become less productive and more anxious. Be intentional. Reach out to your staff. Constantly. Get them to open up. Be there for them.
  • Share the knowledge. We’re all figuring things out. As something you try suddenly works for you, share that with others. The sooner you can pool your knowledge the faster the team and the company will recover and find their new normal.

As a tech leader, in a challenging environment due to the Covid19 pandemic: what are some of the ways in which you are enabling a balanced remote work culture while maintaining motivation levels?!

On many occasions, if I sense an employee is stressed or is over-working due to the circumstances we find ourselves in, I’ve given them paid time off. These are not official vacation days or sick days. This is simply a recognition of hard work and a stated desire to manage their well-being.

Share with them your own personal concerns and challenges. Employees often assume their leaders do not suffer from the same issues they do. They hold their senior executives in high esteem as a result of their success record. Rather than placing yourself on a pedestal, walk amongst your team as a colleague and a fellow human that is challenged. They will respect you more and follow you blindly because they can relate to you.

Tell staff when it’s quitting time. It’s so easy to work longer, or harder, when you’re WFH. Sometimes they need a reminder that it’s okay to stop working despite the home office being nearby.

Recognize employee accomplishments. Share them with the rest of the organization. Give them the accolades they deserve. Gift them with bonuses or meals or perks they desire for a job well done.

Reach out to their significant others and thank them with small gifts for allowing their partners to be such amazing contributors during these uncertain times. Recognizing that there is an impact on not just the employee but also their family will have a dramatic impact.

Manage your expectations. Tell them, whenever you assign them a new task, that you recognize this is outside of their comfort zone or their expertise. Encourage them to embrace the challenge but seek help. Remind them that failure is always an option because even in failure we learn much. Explain the desired outcomes and then let them figure out the required steps to achieve them; they do not need your micro-management in these stressful times.

Constantly ask them how they’re doing. Coach them on how to manage the burden and the stress. Give them permission to not do everything and help them identify which tasks can wait and which tasks are more important.

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The VanillaSoft

The VanillaSoft sales engagement platform helps keep sales team focused on engaging leads and growing revenue with their range of guided selling tools and integrated communications tools.

Darryl Praill is the Chief Revenue Officer at VanillaSoft, the industry’s most established Sales Engagement Platform. As an accomplished award-winning marketer, a Sales World Top 50 Keynote speaker, a 2020 top 10 SaaS Branding Expert, a Top 19 B2B Marketer to Watch in 2019, a social media influencer, a category-leading podcaster, and a serial entrepreneur. Darryl has raised almost $100 million in venture capital, acquired, merged and taken companies public, been hired and fired, and worked for companies of all sizes