Chris Orlob’s Post

99% of SMB sellers think they need to get promoted to enterprise to make $300,000 a year. They're wrong. What they REALLY need is a hungry market and a decent comp plan. Here's 4 reasons why SMB reps can out-earn enterprise reps. 1. If your company isn't firmly "upmarket," enterprise reps struggle. In my heyday at Gong, the highest-earning salespeople were SMB reps. I knew several who cracked $300,000. We had not yet 'crossed the chasm' to selling to the enterprise. Yet startups and SMBs were RAVENOUSLY hungry for what Gong had to offer. Enterprise reps struggled. SMB AEs routinely hit 200% of their number. When you have commission accelerators in place, that's big money. 2. Enterprise customers are "laggards." Again, if your company hasn't "crossed the chasm," most enterprise buyers view new technology with skeptical eyes. They want to see other enterprises "go first." They aren't trying to get a fast-mover advantage. They're trying to not f*** up. It can take YEARS for your company to "crack" the enterprise. 3. Enterprise is feast or "famine." The people who make HUGE incomes in enterprise? They close 2-3 MEGA deals per year. They aren't hitting a bunch of singles, doubles, and triples. They choose to go "all in" on a few home runs. If it pans out, they make millions. If it doesn't, they make their base pay. 4. Your quota in enterprise is much higher. Here's a dirty secret for you, coming from a former sales leader who designed comp plans: If your OTE goes up, so does your quota. Senior business leaders know that quotas must be at least 3.5x to 5x the size of your OTE. It has to be that way. Otherwise the math of the business falls apart. 5. Product/market fit in enterprise and SMB are VERY different. Just because you have product/market fit in SMB doesn't mean that applies to the enterprise. Big enterprises have DIFFERENT demands on your product for it to be considered. SSO and advanced security capabilities to name a couple. Many companies are light on these features. So enterprise reps have to "sell around those gaps," which is REALLY hard. Ok. To the future guy in the comments: I agree with you: There are long-term career reasons to want to land an enterprise sales role, even if it means making less money short term. I support that. But don't tell me for a second that SMB reps are destined to make peanuts and enterprise reps are destined to make millions. Rarely happens that way. Especially in hot startups. You can make $300,000 in SMB if you find a hungry market. P.S. I had dinner last night with the COO of a $2B publicly held SaaS company. He formerly worked at Box in their heyday. Mentioned their highest-earning salespeople were SMBs reps, often topping out at $500k. Something to think about.

Product-Led Growth (PLG) has been all the rage for more than a half decade. But it’s almost impossible to scale to $100MM ARR selling $7/user/month plans and hoping you hit the lottery with the “viral loop”. It’s clear that to really win in PLG, you need to establish an enterprise sales motion to sell large ACV deals to big companies. They pay more, stay longer, sign multi-year contracts, and expand more. They’re usually just better overall customers. The problem is that nobody has really figured out the hybrid motion with PLG and Enterprise running simultaneously. Because the company culture and the GTM metrics favor whichever motion they grew up with, which usually directly inhibits success of the other motion. It happens in both ways. Here’s how: 1) Start PLG -> Add Enterprise Sales The PLG company scales to $25MM ARR with just PLG and now they want to boot up their Enterprise motion. They bring the same mindset and tactical strategy they use to sell a $7/user/month plan to the mid-market and enterprise to sell $100k+ ACV deals to big companies. The metrics and scoring models inside the company are built 100% to incentivize direct response performance marketing (high volume, transactional, easily trackable marketing) which is terribly inefficient and unproductive when marketing/selling Enterprise deals. The strategy really breaks down and typically leads to many many years of struggling to get the Enterprise motion off the ground with slow growth and/or very high CAC. 2) Start Enterprise Sales -> Add PLG The enterprise company gets to $50MM ARR and then they want to add a PLG or “free trial” motion. They now have a large, well-functioning Sales team that gets 200 sales meetings per month from the website. The revenue growth model is totally dependent on this flow. Then the company decides to run an A/B test to add a “Free Trial” button next to the “Get a Demo” button. What happens? -Everyone that used to click “Get a Demo” now clicks “Free Trial” -Nobody converts in the free trial because it was half-baked and not ready -Instead of getting 200 sales meetings from the website that month, they get 10 sales meetings -The whole company panics as metrics fall. They eventually hit abort mission and go back to Enterprise only. ___ It’s easier to start PLG and add Enterprise later IMO then the other way around. But either way, companies still struggle in building out this hybrid motion. I don’t have all the answers to this yet - far from it - but it’s clear there are some fundamental issues in the mindset, metrics, and downstream execution when running this hybrid GTM motion. Even with the big PLG logos that get glorified every day here on LinkedIn don’t seem to really have it figured out. We’re hard at work to build new frameworks & operating models that support this dual motion. Stay tuned as I drip out more findings & progress that we discover from working with these companies in real-life. #marketing #b2b #sales #plg

Product-Led Growth (PLG) has been all the rage for more than a half decade. But it’s almost impossible to scale to $100MM ARR selling $7/user/month plans and hoping you hit the lottery with the “viral loop”. It’s clear that to really win in PLG, you need to establish an enterprise sales motion to sell large ACV deals to big companies. They pay more, stay longer, sign multi-year contracts, and expand more. They’re usually just better overall customers. The problem is that nobody has really figured out the hybrid motion with PLG and Enterprise running simultaneously. Because the company culture and the GTM metrics favor whichever motion they grew up with, which usually directly inhibits success of the other motion. It happens in both ways. Here’s how: 1) Start PLG -> Add Enterprise Sales The PLG company scales to $25MM ARR with just PLG and now they want to boot up their Enterprise motion. They bring the same mindset and tactical strategy they use to sell a $7/user/month plan to the mid-market and enterprise to sell $100k+ ACV deals to big companies. The metrics and scoring models inside the company are built 100% to incentivize direct response performance marketing (high volume, transactional, easily trackable marketing) which is terribly inefficient and unproductive when marketing/selling Enterprise deals. The strategy really breaks down and typically leads to many many years of struggling to get the Enterprise motion off the ground with slow growth and/or very high CAC. 2) Start Enterprise Sales -> Add PLG The enterprise company gets to $50MM ARR and then they want to add a PLG or “free trial” motion. They now have a large, well-functioning Sales team that gets 200 sales meetings per month from the website. The revenue growth model is totally dependent on this flow. Then the company decides to run an A/B test to add a “Free Trial” button next to the “Get a Demo” button. What happens? -Everyone that used to click “Get a Demo” now clicks “Free Trial” -Nobody converts in the free trial because it was half-baked and not ready -Instead of getting 200 sales meetings from the website that month, they get 10 sales meetings -The whole company panics as metrics fall. They eventually hit abort mission and go back to Enterprise only. ___ It’s easier to start PLG and add Enterprise later IMO then the other way around. But either way, companies still struggle in building out this hybrid motion. I don’t have all the answers to this yet - far from it - but it’s clear there are some fundamental issues in the mindset, metrics, and downstream execution when running this hybrid GTM motion. Even with the big PLG logos that get glorified every day here on LinkedIn don’t seem to really have it figured out. We’re hard at work to build new frameworks & operating models that support this dual motion. Stay tuned as I drip out more findings & progress that we discover from working with these companies in real-life. #marketing #b2b #sales #plg

Product-Led Growth (PLG) has been all the rage for more than a half decade. But it’s almost impossible to scale to $100MM ARR selling $7/user/month plans and hoping you hit the lottery with the “viral loop”. It’s clear that to really win in PLG, you need to establish an enterprise sales motion to sell large ACV deals to big companies. They pay more, stay longer, sign multi-year contracts, and expand more. They’re usually just better overall customers. The problem is that nobody has really figured out the hybrid motion with PLG and Enterprise running simultaneously. Because the company culture and the GTM metrics favor whichever motion they grew up with, which usually directly inhibits success of the other motion. It happens in both ways. Here’s how: 1) Start PLG -> Add Enterprise Sales The PLG company scales to $25MM ARR with just PLG and now they want to boot up their Enterprise motion. They bring the same mindset and tactical strategy they use to sell a $7/user/month plan to the mid-market and enterprise to sell $100k+ ACV deals to big companies. The metrics and scoring models inside the company are built 100% to incentivize direct response performance marketing (high volume, transactional, easily trackable marketing) which is terribly inefficient and unproductive when marketing/selling Enterprise deals. The strategy really breaks down and typically leads to many many years of struggling to get the Enterprise motion off the ground with slow growth and/or very high CAC. 2) Start Enterprise Sales -> Add PLG The enterprise company gets to $50MM ARR and then they want to add a PLG or “free trial” motion. They now have a large, well-functioning Sales team that gets 200 sales meetings per month from the website. The revenue growth model is totally dependent on this flow. Then the company decides to run an A/B test to add a “Free Trial” button next to the “Get a Demo” button. What happens? -Everyone that used to click “Get a Demo” now clicks “Free Trial” -Nobody converts in the free trial because it was half-baked and not ready -Instead of getting 200 sales meetings from the website that month, they get 10 sales meetings -The whole company panics as metrics fall. They eventually hit abort mission and go back to Enterprise only. ___ It’s easier to start PLG and add Enterprise later IMO then the other way around. But either way, companies still struggle in building out this hybrid motion. I don’t have all the answers to this yet - far from it - but it’s clear there are some fundamental issues in the mindset, metrics, and downstream execution when running this hybrid GTM motion. Even with the big PLG logos that get glorified every day here on LinkedIn don’t seem to really have it figured out. We’re hard at work to build new frameworks & operating models that support this dual motion. Stay tuned as I drip out more findings & progress that we discover from working with these companies in real-life. #marketing #b2b #sales #plg

Product-Led Growth (PLG) has been all the rage for more than a half decade. But it’s almost impossible to scale to $100MM ARR selling $7/user/month plans and hoping you hit the lottery with the “viral loop”. It’s clear that to really win in PLG, you need to establish an enterprise sales motion to sell large ACV deals to big companies. They pay more, stay longer, sign multi-year contracts, and expand more. They’re usually just better overall customers. The problem is that nobody has really figured out the hybrid motion with PLG and Enterprise running simultaneously. Because the company culture and the GTM metrics favor whichever motion they grew up with, which usually directly inhibits success of the other motion. It happens in both ways. Here’s how: 1) Start PLG -> Add Enterprise Sales The PLG company scales to $25MM ARR with just PLG and now they want to boot up their Enterprise motion. They bring the same mindset and tactical strategy they use to sell a $7/user/month plan to the mid-market and enterprise to sell $100k+ ACV deals to big companies. The metrics and scoring models inside the company are built 100% to incentivize direct response performance marketing (high volume, transactional, easily trackable marketing) which is terribly inefficient and unproductive when marketing/selling Enterprise deals. The strategy really breaks down and typically leads to many many years of struggling to get the Enterprise motion off the ground with slow growth and/or very high CAC. 2) Start Enterprise Sales -> Add PLG The enterprise company gets to $50MM ARR and then they want to add a PLG or “free trial” motion. They now have a large, well-functioning Sales team that gets 200 sales meetings per month from the website. The revenue growth model is totally dependent on this flow. Then the company decides to run an A/B test to add a “Free Trial” button next to the “Get a Demo” button. What happens? -Everyone that used to click “Get a Demo” now clicks “Free Trial” -Nobody converts in the free trial because it was half-baked and not ready -Instead of getting 200 sales meetings from the website that month, they get 10 sales meetings -The whole company panics as metrics fall. They eventually hit abort mission and go back to Enterprise only. ___ It’s easier to start PLG and add Enterprise later IMO then the other way around. But either way, companies still struggle in building out this hybrid motion. I don’t have all the answers to this yet - far from it - but it’s clear there are some fundamental issues in the mindset, metrics, and downstream execution when running this hybrid GTM motion. Even with the big PLG logos that get glorified every day here on LinkedIn don’t seem to really have it figured out. We’re hard at work to build new frameworks & operating models that support this dual motion. Stay tuned as I drip out more findings & progress that we discover from working with these companies in real-life. #marketing #b2b #sales #plg