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Comment by chevman | Hacker News Reader

I work at a company within the Fortune 10 and we use Twilio in some isolated products, and they are pushing hard on a few potential deals/opportunities to expand further.

Technical foundation appears solid to all their stuff, but their enterprise sales/account folks seem very green - unsure of how to navigate large enterprises, not connecting with the right folks at the right level within the org, not understanding who or how decisions are getting made, etc.

We see this alot - deals with tens or potentially hundreds of millions of dollars at stake where potential vendors have a couple sales folks working the deal, not getting traction. Get a few more folks working the deal and figuring out the right angles and they could have it locked down in a matter of months, but they never seem to figure this out and a year later they're still dicking around with the wrong people at the wrong level not making progress.

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I work in sales at Twilio and manage the account of a huge enterprise customer. We've sold to a few of their departments and what we've done so far has been successful.

But every time I call my contacts at this customer, something seems to derail us from the path to further integrations. They know our products work and save them money. But just last week I called Glenda in accounting only to find out her phone number now goes to some guy named Bob who refused to tell me what desk he works on or what happened to Glenda.

So I fired off a quick email to Vincent, the CIO, asking for an updated contact list since Glenda is gone and I heard Sally moved to outside sales. Vincent's secretary wrote back to me saying she'd "ping" him and "circle back". That was two weeks ago.

Last year when we closed a bunch of deals with this company I was recommending to my management that we spend even more effort to get further with them this year. But here I am halfway through the year and I feel lucky that my proposal was turned down because we were already too busy with other clients. What would another sales guy have done anyway, apart from dogfooding our sweet new IP phone stack as he wasted his time trying to navigate an endless megacorporate morass?

Do you guys have top tier enterprise sales guys? Maybe people in their 50's and 60's, who have a lot of contacts, and relate to C level people better than millenials? Is commission capped or uncapped? By uncapping commission sales is driven to maximize deal size and be hardcore about closing, even if that means one guy gets a $700k bonus. He still brought in way more!

Really solid enterprise sales guys see the corporate morass as a challenge and have developed and learned tricks to overcome it. It's a very psychological game. You need to create urgency, you need to think up reasons to call, reasons you need meetings. For a huge, fortune 100 client, you should treat the sale as an orchestrated project, not something you casually shoot an email off to and forget about for 2 weeks

Without more context, my suggestion is to sell to the CIO instead. You are already in contact with him. Get him to initiate a project.

Blueprint-sell, solution-sell, or whatever is the current hotness in enterprise software nowadays :)

Joke-aside, engage with the CIO. If the current sales rep thinks he or she is too "low-level", involve someone higher up in your company, get the VP of sales involved. Hell, get your CTO, chief architect and/or CEO involved. CEOs make great salesmen in enterprise software. Get the CIO and higher ups excited about using Twilio throughout the organization. If you want to hit it big, don't start from the bottom (only). Start from the top.

As for this problem:

> since Glenda is gone and I heard Sally moved to outside sales. Vincent's secretary wrote back to me saying she'd "ping" him and "circle back". That was two weeks ago.

Build a sphere of influence and expand on it. I found out the hard way that it was absolutely terrible for me that I had only 1 or 2 points of contact in a company. What if they moved on (suddenly)? Build contacts within the company, and expand. Keep in contact with them.

What kind of salesperson waits two weeks for a low level functionary to get back to him instead of forcing the issue himself?

I see this a lot at start-ups as I come from automotive (similar to large enterprise sales, engineering teams with product teams make calls on buying 10's of M to 100's of M in product.)

The biggest problem I see is you're not on site. You're not there physically and haven't met Glenda and her manager or immediate peers. Because if you were on site Glenda would've let you know she's thinking of leaving and would've referred you to her manager in charge of her replacement. There's so much gained in just showing up and being present.

It doesn't feel scalable or meritocric but it is how a lot of humans work.

Are you telling a Twillio sales rep that you can't do proper enterprise sales by phone ? Life is hard ;)

It's really interesting to hear you say that. I'm in sales and have to make decisions like this all the time. On our side we're constantly making calculations about which accounts to invest our resources in. It's really hard! There are so many variables. We're acting on imperfect information. We're considering the other accounts we're working on, and doing a cost benefit analysis.

Bigger companies like MSFT and Oracle are usually better at this because a) they've been doing it longer, b) they have more resources to burn. If they throw 10 people on a large deal and it doesn't go through the company itself typically isn't hurt that much (the reps, that's a different story).

The decision to put that many resources on an account that may or may not bring in revenue in the short-term is an enormous decision for a company like Twilio. This is the hard part that they have to go through. Trying to place the right bets on the right accounts. Sounds like they may have gotten your account wrong, unfortunately.

>>> b) they have more resources to burn. If they throw 10 people on a large deal and it doesn't go through the company itself typically isn't hurt that much (the reps, that's a different story).

Basically, you're saying that your company is flimsy and doesn't have the resources to execute a sale. It's probably not the impression you want to give to clients ;)

MSFT/Oracle win because they have a) decades of experience in selling b) branding c) already in the door of most companies.

Did I strike a nerve or something? The personal insult makes you look defensive.

And no, that's not what I'm saying.

What I am saying is self evident. Large companies have more resources to spend, and they do. Smaller companies have less to spend, which results in experiences like OP's, as they have to pick and chose their battles more selectively. MSFT has laid off more sales staff in the last year than Twilio employs.

Have you ever thought of helping them out?

I mean if (1) what you say is true, (2) you have the know-how and ability to navigate such structures, and (3) you can build a team that closes these deals, then I'm positive Twilio would spend a small fortune to hire you.

Why not explore that route?

Lol, knowing the route means you can do the job.

Slicing through middle-men, lol

(4) and that Twilio agrees with this argument.

Sort of a roundabout way of saying that since Twilio is currently dropping the ball... they're not apt to pick it up now.

They also compete with themselves.

It's pretty easy to figure out the bottom dollar when people repackaging their services show up.

I'm not familiar with "bottom dollar" used in this way--could you help me out?

"bottom dollar" probably means the cheapest price. When resellers come, then the prospective customer can gain more knowledge through the bargaining and negotiation process. This is bad for Twilio salespeople because they can't push for a higher price.

It's SMS in the USA, it's a low price high competition industry.

I never understood this. Why do companies cut deals for services like twilio offer? Fair & progressively discounting pricing backed by a market leading product would save on sales salaries and commissions while increasing deal flow. I understand the corporate culture around deal making is also too ingrained on the buyers side too however it's long term detrimental to all parties involved. Everytime I've been involved in this type of exchange the only thing on my mind is how useless and irritating the sales team are, while i wonder about competitors with up front pricing who will help speed up delivery of the actual feature /product.

Short answer: dunno.

Other answer: do you optimize every aspect of your life? I highly suspect a large company run by humans would do that.

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