software engineer

account executive

senior software engineer

sales representative

solutions engineer

Twilio

Enterprise sales has seen a high amount of turnover in the last year due to a recent re-org regarding territories and account strategy. Many reps are facing extremely high quotas with either few strategic accounts to work or a large number of greenfield accounts that are not "ideal" Twilio targets (i.e. not tech forward, B2B, small number of customers, etc.). Twilio is facing some challenges bridging the gap from just a messaging company known for SMS and voice to a software company, with products like Flex, Segment, and Frontline. I'm confident Twilio will get through it and continue to iterate quickly as it has always done, but as of right now there is a huge uphill battle in the enterprise sales segment as we figure out new ways to break into tech-laggard, legacy enterprise organizations.

I imagine many of the teams are very happy to be there and truly enjoy what they are doing. I worked in the IT department where there was gross abuse of the unlimited PTO policy for the few Full-Time employees. Most of us were contractors being promised "conversion" full time repeatedly. I understand there are many factors that I was not aware of, but it was not a good experience for me. I think others may have a difference of opinion. That said, my experience was that there was a lot of competition and in-fighting amongst the team. That said, I wish them the best and I have no doubt that the team will get better as my old manager gets more experience. I learned a TON and am still grateful for the job skills and experience.

Leadership at Twilio consistently fails to execute or craft a coherent strategy. Instead, they rely heavily on consultants who repeatedly recommend cutting jobs and rehiring offshore, leading to a vicious cycle of instability and distrust among employees. This approach not only undermines morale but also erodes the company’s ability to innovate and retain top talent. If you dare to challenge senior leadership or question their decisions, you’re quickly managed out—creating a culture of fear and compliance rather than one of collaboration and growth. Leadership appears more focused on short-term cost savings and maintaining control than fostering a sustainable, high-performing culture, leaving teams overburdened and undervalued.

Life as a Twilion is not bad.  It was easy to navigate and the option to earn your red track jacket was a great cultural norm that I gladly partake in.  I loved this because my role was not technical, but I was still able to showcase my ability in a Software org.  The culture was very laid back and relax, with an open communication policy.  It opened my eyes to how exciting the Software Industry is and I would def recommend for others.  When I initially started there were lots of monthly perks and incentives to get together with fellow Twilions.  These last 12 months have been so brutal.  Hard to tell what the future will bring. 

What is the best part of working at the company?
Used to have smart, forward-thinking talent

What is the most stressful part about working at the company?
Shameless leadership team that stashes their pockets
Lack of strategic direction. Vision is strictly a set of marketing slogans
Superficial, form over substance mentality

What is the work environment and culture like at the company?
Lots of lip-service to DEI but not a data-driven company
Lack of decision-making principles
Mediocrity rules

What is a typical day like for you at the company?
Constant meetings
Lack of decision-making, or sticking to decisions
Short-term mentality that drives minimal progress

The first couple of years at Twilio were great. I genuinely felt like I was going to stay for the rest of my career. However, bad management in the finance department and even worse management changes has made working in finance unbearable. I've seen white males get promoted to directors and above while others, who brought more value were not because they were not white. There were surveys sent out every year about management, career path salary, and I know that finance employees responded honestly but nothing has been done. To this day, friends in finance leave the moment they see daylight.

I would recommend this job to anyone who has a drive to help and enjoys being behind perpetually. 

I don't mind that feeling at all and I enjoyed this job more than any before. It was my dream job. 

The manager I had was not fond of me and as such, I lost my job. 

No one should have that much freedom in any company but by the time I realized what was happening, it was too late. 

Shame because its been my biggest loss in life so far.

Twilio relies heavily on contract workers. After being told I would get a chance to move up, that was denied me due to headcount/corporate semantics. Understandable, however, very inconvenient. The culture was exceptional, with a heavy emphasis on Employee Experience. As an Ops Assistant I got to know people all over the office. It was a lot of physical labor and walking around which gave me an opportunity to meet a lot of folks from different departments. Overall it was a great experience, with a bit of a disappointing ending.

The executive team is in flux.  The CEO has just been replaced, but it may be a little too late for Twilio.  Mismanagement has not allowed the sales organization to be properly staffed and supported.  The customer success, sales, and other teams have been dismantled through a series of three different layoffs.  It feels like the company is being prepared for a sale as a whole or broken off into pieces. 

I would warn anyone looking to work at Twilio to ask serious and hard questions to the interviewer(s).

Exciting company to work at with products that employees and developers alike believe in. Even though the company is experiencing growth, it retains a startup culture and the opportunity for employees to grow into new roles and/or new teams. I love my team and coming into work every day.

Top Job Titles	Average Salary
Software engineer 42 salaries reported	$159,823 per year
Account executive 11 salaries reported	$139,755 per year
Senior software engineer 15 salaries reported	$174,389 per year
Sales representative 3 salaries reported	$60,000 per year
Solutions engineer 1 salary reported	$152,000 per year

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