Dec 30, 2021 · 38m · saastr
How to Scale Outbound Sales with the CROs of Outreach, Malwarebytes, HubSpot, Seismic
Anna Baird · 13m spoken Michelle Benfer · 8m spoken Amy Appleyard · 6m spoken Tony Benvenuto · 5m spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
At SaaStr Annual, top sales executives from Outreach, HubSpot, Malwarebytes, and Seismic share actionable strategies for navigating hiring shortages, developing and retaining early sales talent, fostering cross-functional alignment, and scaling diverse go-to-market organizations.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 6.2 Guest teaching 0.3 Guest disagreement 0.2 Jason pushing back 0.2
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 28:35 Advocating for sales placement over marketing
Michelle Benfer politely but firmly pushes back on placing BDRs in marketing, maintaining that sales culture, repetition, and excellence require them to sit strictly within sales.
Hardest push from Jason ▶ 26:06 Reframing underperformers as success storiesBaird immediately re-centers Michelle's playful phrasing of PIP recipients as 'losers' by affirming that turning around performance makes them notable success stories.
Biggest teaching moment ▶ 8:28 Compensation plan mechanics at HubSpotMichelle Benfer explains how HubSpot structures quotas so company targets are met at 110% rep attainment rather than the conventional 80%, providing a key hiring differentiator.
Jason holds their own ▶ 14:58 Detailing Outreach structured SDR levelingBaird explains how Outreach designed clear stage progressions from SMB to enterprise SDR and built a 5-week preparatory program for AE promotions.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Panel Introductions and Early Career Sales Advice | 6 | 0 | 0 | 0 | Anna Baird moderates the opening segment seamlessly and shares her own practical experience landing a $600k deal from her first cold call to Symantec, complementing the panelists' advice on authenticity and resilience. | |
| Navigating the Sales Talent Shortage and Modern Hiring Strategies | 5 | 1 | 0 | 0 | Baird prompts the panel on the macroeconomic sales labor shortage, framing the topic with Wall Street Journal data before Tony, Amy, and Michelle elaborate on risk aversion, compensation structures, and non-traditional hiring. | |
| Career Development, Engagement, and Retaining Early Sales Talent | 7 | 0 | 0 | 0 | Baird demonstrates extensive expertise by explaining Outreach's internal SDR-to-AE progression tracks and weekly training programs, reinforcing and synthesizing the panelists' ideas on mentorship and career paths. | |
| Organizational Alignment: Sales vs. Marketing and Deal Management | 7 | 0 | 1 | 1 | The panel explores organizational placement of BDRs between marketing and sales; Baird contributes Outreach's unified weekly cross-functional pipeline governance model to emphasize holistic funnel ownership. | |
| Reimagining the SDR Function with AI and Deep Mentorship | 6 | 1 | 0 | 0 | Baird introduces an unscripted question regarding structural changes to the SDR role. She and the panelists exchange strategic recommendations ranging from propensity AI modeling to having junior reps shadow customer QBRs. | |
| Advancing Diversity in Sales Leadership and Concluding Thoughts | 6 | 0 | 0 | 0 | Baird highlights Outreach's targeted DEI initiatives and newly launched RISE leadership program to coach women managers into VP positions before closing out the panel. |
Statements from this episode (13)
Benfer: Refuses to open sales emails unless they are personalized
“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.”
Baird: First cold call voicemail resulted in $600,000 deal with Symantec
“Early my, I still remember vividly my very first cold call. Yes. It was to Symantec, so those of you know, they're like, here in the valley, virus, anti-virus software and I was scared to death. I still remember, like, literally not breathing when I left the v…”
Benvenuto: Predicted early 2022 sales talent market would become saturated
“I think come January, February timeframe, we might be in a completely different, ah, situation where the talent is saturated and everybody's ready to make a move.”
Appleyard: Spending One Year in an SDR Role Benefits Any Career
“You'll never regret, even if you just spend a year as an SDR or BDR, whatever you want to do for the rest of your career, you will always benefit from it, and I think just helping to encourage people to take that risk, like, seeing it as a path to anything. It…”
Appleyard: Sales reps rarely leave cybersecurity once they pass one year
“In the cybersecurity industry, you often just need to spend a year just understanding the industry, and once you've learned all of that, even if you don't want to be a salesperson, you usually don't want to leave the industry.”
Baird: Outreach runs a five-week transition program preparing SDRs for AE roles
“We also have them doing a, there's a five week that they get nominated into preparing them to be an SMB AE, so our small business AE team. They have a five week, they get nominated into it, they get to work with the AEs, they get to learn what that's like, pre…”
Benvenuto: Having SDRs shadow AE deals directly improves lead pipeline quality
“We love the mentor system or buddy system, if you will, and allowing them to get deeper and really ride shotgun on a deal... SDRs and BDRs typically don't dive deep in any type of you know, demoing or, you know, procurement cycles, things like that. Negotiatio…”
Benfer: HubSpot holds forums for employees who beat PIPs to boost retention
“We also highlight for lack of a better word, the losers, but the people who have been on performance plans, and they've beat them, and they've gone on to succeed and become managers or directors, so we do these forums of people that were very close to being le…”
Benfer: BDR teams should sit within sales, not marketing
“I'm a firm believer of the center of excellence that should live within sales. Nothing against my friends in marketing, but I do think there is a sales culture and a level of repetition that I think is beneficial to keep the BDR organization in sales.”
Benfer: Predicted in 2021 that sales teams would adopt AI by 2024
“It actually is a cost saver, and you're not going to be so headcount reliant the more system intelligence that you have to feed your team. So, That's what I would change, because we're still in too much of a manual process, and there are incredible tools out t…”
Appleyard: Mandating Deal Shadowing for SDRs Accelerates Account Executive Ramp Times
“Like it happens maybe because it's a big deal or because somebody is being mentored, but if that were actually built into the program, you would need more SDRs because they would have less time and, But I think if you did that, it would make the ramp time into…”
Appleyard: SDR hiring is the biggest lever for company-wide diversity
“As any sales leader knows, especially if you have an SDR organization, if your company has a goal of changing sort of the composition of the organization, we hire so many people in sales, and they, we hire them in so much in that entry level role, and they can…”
Baird: Outreach launched a 9-month VP training program for women managers
“We also just started, we launched it this week, it's called our RISE program, so I'm taking our women's And sales managers and teaching them how to be VPs. So I think we're, I'm doing a small group. They're a, they're my guinea pigs. We're going to take them t…”