The CEOs ability to run through 3 CROs in the last 2-2.5 years, with many more fires, hires, layoffs, mass exits, HUGE turnover (outside of engineering) is indicative of systemic issues making this organization close to good but not quite.
-Most of leadership is mediocre, talk a big game but no results, lack experience, "yes" men, come from dying companies, and or are un-professional (for example a leader having an extramarital affair with a subordinate, and it being witnessed)
-No one but 1-2 people hit quota, and enterprise reps creep or close deals commercial reps should be closing
-Excluding young SDRs who are shoved into churned AE roles, no one gets promoted or gets raises
-CEO and leadership think the product sells itself, and under value sales reps and or fire directs without taking a look at management
-Marketing & sales continuously fail to capitalize on the unique platform which means there is little to no market presence or brand awareness outside of the Bay
-Google decided to turn GoogleVoice into a business product offered with their productivity suite, and are slowly eating Dialpad's messaging and lunch
-Marketing funnel dried up and all the new marketing team did was replicate the old marketing team's effort, lots of unnecessary trial and error = waste of $$$
-Overspend on over produced videos that fail to garnish much attention or appeal
-Tons of fake, under qualified marketing leads with new and old marketing team
-Many hate coming in but try to make it enjoyable by developing social cliques, which breeds problems and compounds the culture problem
-Since all of the experienced sales people left (whoever is left is on the prowl) the teams have been filled with inexperienced reps who accept lower pay to get a shot at being a sales rep and build their resumes to go somewhere "better"
-If you went to UC Berkeley, you have a 99% chance of being hired because it's the CEOs alma mater and the "good old boy" system is very real.
-Although there's money being thrown every which way, don't expect to be paid more than average unless your boss has significant pull...if you're filling a sales role they like to under pay (they'll brag about the savings they made off you) and if they move quickly with you chances are you are very green so take the job
-Commission rates (to my knowledge) are less than other technology companies especially in startup land
-Gong and Chorus are more mature, has better marketing, way more customers, and a better market fit than the AI company Dialpad acquired
-Super slow sales cycles, one big logo took over 2 years to close in enterprise, commercial usually takes a year
-There is a lot of discrimination and odd practices (resignations and lawsuits) in this workplace, maybe an indicator to the General Counsel's un-announced leave from the company after 3.5 years
CEO and leadership brag about VC money, and how much they need to burn so they do the following:
-buy software licenses for unnecessary platforms when we did well before without them
-channel team spends lots of money partying, on alcohol or food trying to buy favor and not viewed well (huge channel sales pipeline compared to actual closed revenue)
-marketing spending money on silly efforts like wrapping buses and billboards which are capital intensive and specific only to the bay
-doubling the size of the sales team although sales were struggling before
-swapping in and out of learning management software
-vastly over hiring for non-crucial/admin roles (engineers could use more help while sales and marketing figure it out or start getting close to their actual quotas)
-spending tons of money on SKOs and getting drunk with investment partners
-hired a full sales operations team that reinvented the wheel
-expanded HR team to combat culture issues not realizing culture starts with leadership
-pay or arrange to have themselves on "great place to work" lists or "fast growing startups" lists to hoodwink prospective talent and for Bay area "bragging rights"
-VC cash allows them to hire fast, fire faster.