How to Scale Outbound Sales with the CROs of Each (Podcast 513 and Video)


Scaling your sales team can be one of the hardest things to do in SaaS. When do you hire for outbound? How can SaaS companies retain BDR/ SDR talent? What’s the best way to help your sales team navigate today’s changing markets and changing priorities? And what’s the right time to fill crucial sales leadership roles?

Amy Appleyard, SVP Global Sales at Malwarebytes, Michelle Benfer, VP, Head of North America Sales at HubSpot, Tony Benvenuto SVP of Sales West at Seismic and Anna Baird, CRO at Outreach share the lessons they learned when scaling their outbound sales teams.

#1 Buyers Expect Personalization in Outbound Sales

BDRs (business development representatives), SDRs (sales development representatives) are mainly responsible for opening up new pipeline and sourcing outbound revenue, usually via email. So why do most sales orgs spend the least amount of training reps that are your company’s first encounter with a potential new customers?

Michelle Benfer, VP, Head of North America Sales at HubSpot emphasized training for personalization: “Don’t be a robot. I think for many of us who are overseeing young sellers, BDRs; I get so much robotic email every single day. And you can just tell it is a sequence that they copy, paste, pump out. And I don’t open anything unless it’s personalized. So be unique. Don’t be a robot. Cut through the noise.”

Anna Baird, CRO at Outreach reminds us all not to overlook a good cold call with this example: “I still remember vividly my very first cold call. It was to Symantec (antivirus software), and I was scared to death. I still remember literally not breathing when I left the voicemail because it went to voicemail but still ended up with a $600,000 deal out of that. So don’t be afraid to just put yourself out there because you just never know what’s going to happen. Depending on who you’re calling, and you never know what is on the other end of the line. I think with all the social media we have out there, it’s way easier to understand what your buyers are looking for and make sure you know that, too.

Know something about their business, do your research. I think that is the biggest advice on the customized side where all the buyers are expecting you to do that, and that whole journey with buyers has changed, especially these last couple of years.”

#2 Don’t Overlook Development for Sales Development

SDRs and BDRs can be your secret weapons in outbound SaaS. The whole category exists because many SaaS companies are really bringing hyperfocus onto those roles into the market. So now what? Sales and business development roles are looking for development, right? How should you foster growth and scale from your current pool of SDR and BDR talent?

Amy Appleyard, SVP Global Sales at Malwarebytes shares how they retain talent: “When you’re bringing in SDRs into an organization, you’re hopefully growing the talent to stay in sales, but keep in mind it doesn’t always happen that way. Often, 70ish percent of the time they do, but maybe they’re just more interested in HR or in recruiting or in working in marketing. There are all kinds of paths that they could take. The goal is to keep them at the company.

Tony Benvenuto, SVP of Sales West at Seismic, added that communicating a dedicated, and clear path from BDR/ SDR to AE is crucial: “Going from BDR to an AE, we love the mentor system or buddy system. And allowing them to get deeper and really ride shotgun on a deal. ‘Hey, I’ve thrown over this potential opportunity over the fence, but now I’m going to ride shotgun and be a fly on the wall and hear exactly what goes on to get something across the line.’ SDRs and BDRs typically don’t dive deep in any type of demoing or procurement cycles, things like that, actual negotiations.

You let them ride shotgun and hear this front to back? All of a sudden the light bulb’s going to go off. I throw over higher quality, it’s not so much a volume game anymore, and I’m invested. I want to make my AE shine because then inevitably, I’m going to be the next wave of AEs that are going to come in and dominate.”

#3 How to Retain Outbound Sales Talent

Each of the leaders of Outreach, Malwarebytes, HubSpot, and Seismic all agreed that one of the toughest parts of sales right now is retaining the BDR/ SDR talent you just trained from the ground up. Their advice for hanging onto talent?

  1. Recognition
  2. Spiffs
  3. Foster teamwork on the outbound sales team
  4. Clear career paths forward within Sales (or the organization as a whole)


Key Takeaways

  • Set up dedicated training for incoming outbound sales reps
  • Promote from within
  • Offer professional development and new career opportunities to retain entry-level sales reps 
  • Leverage BDRs to scale your outbound sales

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