What are sales commissions like at Datadog?

Tons of flexibility, great commission

As the size of the organization grew, less flexibility and different culture

Product is market leading World class sales playbook and enablement e.g. MEDDPICC, COM Talented and driven people Flexible WFH balance

Less than 10% of reps hitting Quota across EMEA Enterprise teams due to AOV relative to Quota being too small, ave deal cycles are 4 months so expanding accounts and making good commission takes time

Product is world class and best of breed if you can get companies to buy into total platform approach for observability.

Sales culture is unbearable, around the clock micro-mgmt, BDR metric driven operating model, and completely unrealistic quota expectations for how the GTM is set up. Maybe 10% of sales reps are hitting quota, after the 9 month ramp period is over expect that to be the last commission you receive and if you haven't cracked a whitespace account by then expect mgmt to turn the heat up and make life miserable to force you out. The products are great all together, but if customers want to only purchase or implement one of the main products they struggle to stand out on their own against competition. The billing and pricing model they have in place is designed to entrap customers and get them to have overages on a monthly basis and they then send you to go bill collect every month. Whole separate sales organization internally who handles the largest enterprise customers and make no commission so purely whitespace hunting. Leadership/Founders mantra to sales folks is literally "Dont F*** It Up" as they think the product is so amazing all we can do is screw it up when talking to customers.

free lunches 3 times per week, fairly solid benefits, fun coworkers, good views from the office.

Complicated billing model that punishes customers Clueless leadership that doesn't act on suggestions or advice from employees "Leadership" likes to hire their friends for management roles (friends that have no idea how to manage a team). Some of these managers will ignore slack messages, ignore 1 on 1 meetings, have zero knowledge or advice for dealing with customers, and will spend their time fraternizing in the office while making plans to take more of their unlimited PTO, while they work to wrongly remove and ostracize people on their team. Zero coaching or strategy provided by managers - CSM's are expected to figure things out by themselves Managers will talk and pick and choose their "favorites" will treating others like they don't exist. Promotions are incredibly hard to come by, most CSM's will remain in their same roles regardless of how well they perform. Datadog even pays less for a CSA role that does the exact same role as a CSM. Excessive layers of approval to get out quotes or oder forms to customers. At least 10 different Datadog employees need to sign off before anything is executed. Severely understaffed on the "deal desk" team. Waiting weeks for order forms and then being punished when renewals are late. Base pay and commission are split. Commission checks are received quarterly and are never discussed with the employee. Did you lose $600 from your commission check? You will not get an explanation. I was told that these bonuses are subjective and that managers can pick and choose how much they want to pay and do not have provide any explanation. What kind of company can't even share a commission breakdown for work that's already been completed? This place is everything that's wrong with tech and the corporate world. More money, more money, more money, zero focus on employee development and culture. Some of the worst culture I've ever been a part of, absolutely disgusting.

very complex product -> excellent training CoM and MEDDICC --> excellent sales school

drastic change of company values, climate reflecting in several actions that are questionable throughout, lack of loyalty, support, appreciation by leadership good pay as SDR AE targets not easy to achieve, low commission, low pay

MEDDIC Playbook company KPI driven mindset You don’t get punished on negative bookings

For a sales person it’s most important to earn your commission and get your rewards. I learned that for this companythe most important things Is how to squeeze out the most revenue by paying no or less commission. The chances to make your quota are limited. Only 1-3 out of 30 make their number.

"unlimited" PTO (although grind culture is encouraged), lunch provided 3x a week, snacks, coffee, etc in office

Commission is not based on meetings, it is based on "opportunities" that are up to an AE's discretion if they are considered an opportunity or not. Bros help out bros. Those who are favored do much better than those who are not

Working at Datadog offers several genuine advantages, particularly for sales and customer-facing professionals. The company is undeniably a market leader with an exceptional product that practically sells itself - this makes customer interactions enjoyable and builds confidence in what you're representing. The product's complexity provides an incredible learning opportunity that develops sophisticated sales skills transferable anywhere in enterprise software. The team selling approach is excellent for professional development. Working alongside Sales Engineers, deal desk, and cross-functional teams teaches you the full sales cycle and how to navigate complex enterprise deals. For tenured employees, there are genuine career growth opportunities, and the company does generally promote from within when possible. The c-suite stands out as experienced professionals who understand how to run a successful public company. They're actively involved in operations and customer relationships, bringing a level of strategic thinking that's reassuring. The equity component remains strong given Datadog's consistent public market performance, and the product's stickiness creates a stable business foundation.

The culture has noticeably shifted post-IPO. What was once a growth-focused but balanced environment has become "growth at all costs" with a heavy emphasis on recent performance over long-term contributions. There's a pervasive "what have you done for me lately" mentality that can be demoralizing. Compensation structures, particularly in customer success roles, haven't evolved with market standards or job responsibilities. Many roles function as account management but lack commission structures or meaningful upside potential. Leadership often refers to CS at Datadog as their "secret sauce" which, given the compensation model, feels disconnected from market realities. Chronic understaffing affects both employee experience and customer outcomes. Supporting functions like deal desk are consistently behind hiring goals, creating bottlenecks that impact everyone. The company tends to be inflexible with new leadership - if you're hired as a leader, expect to adapt completely to existing processes rather than bringing external best practices. The work environment has become increasingly rigid. Heavy email culture with excessive documentation requirements slows decision-making. The hybrid policy includes location tracking with monthly reports to leadership about office attendance, which feels micromanaged for professional roles. Compensation bands are inflexible, with minimal annual increases regardless of performance. Turnover has increased across all levels, often because leadership protects existing structures rather than developing talent or addressing systemic issues.

free lunches 3 times per week, fairly solid benefits, fun coworkers, good views from the office.

Complicated billing model that punishes customers Clueless leadership that doesn't act on suggestions or advice from employees "Leadership" likes to hire their friends for management roles (friends that have no idea how to manage a team). Some of these managers will ignore slack messages, ignore 1 on 1 meetings, have zero knowledge or advice for dealing with customers, and will spend their time fraternizing in the office while making plans to take more of their unlimited PTO, while they work to wrongly remove and ostracize people on their team. Zero coaching or strategy provided by managers - CSM's are expected to figure things out by themselves Managers will talk and pick and choose their "favorites" will treating others like they don't exist. Promotions are incredibly hard to come by, most CSM's will remain in their same roles regardless of how well they perform. Datadog even pays less for a CSA role that does the exact same role as a CSM. Excessive layers of approval to get out quotes or oder forms to customers. At least 10 different Datadog employees need to sign off before anything is executed. Severely understaffed on the "deal desk" team. Waiting weeks for order forms and then being punished when renewals are late. Base pay and commission are split. Commission checks are received quarterly and are never discussed with the employee. Did you lose $600 from your commission check? You will not get an explanation. I was told that these bonuses are subjective and that managers can pick and choose how much they want to pay and do not have provide any explanation. What kind of company can't even share a commission breakdown for work that's already been completed? This place is everything that's wrong with tech and the corporate world. More money, more money, more money, zero focus on employee development and culture. Some of the worst culture I've ever been a part of, absolutely disgusting.

Commission is great, product is best in class

Work life balance is not great