A sales rep forgets to pause an email sequence

Published: Wed, 12/10/25

Updated: Wed, 12/10/25

December 10, 2025

TOGETHER WITH

Good morning Quota readers of all stripes (what the heck does that even mean?!) We have another fantastic issue for you this week, with the history of Siebel Systems—the first big-time CRM—followed by Fails, advice, numbers, and more. Sit back and enjoy the show!

NUMBER OF THE WEEK

1 trillion

Lost productivity and poorly managed leads cost companies at least $1 trillion every year

Source: Marketo

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

Microsoft stock tumbled more than 2% last week following reporting from The Information that the tech giant has lowered sales quotas for its AI software after multiple Azure teams missed growth targets in fiscal 2024. The rare quota reduction signals potential headwinds for enterprise AI adoption just as Microsoft doubles down on artificial intelligence across its cloud platform. You can read more about it here.
A 28-year-old door-to-door salesman was arrested in Troutdale, Oregon on Tuesday after accusations that he bit a sheriff’s deputy twice in the hand. The salesman, who was allegedly soliciting without a permit, was asked to leave the area by police. But after coming back and being confronted by a County Sheriff’s deputy, the man attacked and bit the officer on the hand. You can read the full story here.

FEATURE

Amanda Rollins in Switzerland

The First CRM: How Siebel Systems Shaped Modern Selling

In the late 90s, a typical enterprise sales meeting began with a projector warming up, a room full of executives shifting in their chairs, and a consultant opening a laptop that sounded like it might lift off the table. The laptop ran Siebel. The interface looked intimidating, the demo always froze once or twice, and no one in the room agreed on whether it would actually make selling easier. But they all agreed they needed it.
But to understand how the CRM became central to selling, you have to understand how people sold before it.

Notebooks and Hope

Before Siebel, sales organizations functioned like small, isolated departments. Reps tracked deals in notebooks or personal spreadsheets. Managers built forecasts by asking reps to rate their gut feelings. Customer data lived in filing cabinets, personal Rolodexes, and the heads of whoever happened to be employed that quarter.

When a rep quit, they often took the entire customer relationship with them. If a prospect moved from early interest to late-stage evaluation, the only record of that journey lived in an AE’s handwritten notes.

Companies had no unified view of anything. If you asked a VP of Sales for a pipeline update, the answer ranged from optimistic storytelling to pure invention. In that environment, the idea of a system that captured everything in one place sounded like an impossible luxury. Tom Siebel thought it could be real.

Tom Siebel Sees the Future

Siebel began his career at Oracle, and by the late 80s he had built a reputation as a talented, aggressive operator who understood how software could transform large enterprises. He also clashed with Larry Ellison often enough that his departure felt inevitable. When he left Oracle in 1993, he took with him an idea that Oracle had not prioritized: software built specifically for sales teams.

He founded Siebel Systems with the belief that companies needed a dedicated platform that organized customer information at a level no spreadsheet or homegrown database ever could. In theory, the idea was simple: record every contact, track every deal, document every interaction, and surface everything for leadership. In practice, it required complex software, long implementation cycles, and a level of organizational change that many companies resisted.

But once one major company adopted it, everyone else followed. No executive wanted to be the last person running a national sales team from a pile of paper reports.

The Climb to Dominance

Siebel Systems grew faster than almost any software company of its era. By the late 1990s and early 2000s, Siebel became the default choice for enterprises in finance, telecom, pharmaceuticals, manufacturing, and tech.

The product itself was powerful but famously difficult. Installing Siebel often required an army of consultants. Customizing it meant long meetings, long invoices, and long nights for IT teams. Reps complained that updating fields interrupted their flow. Managers loved the visibility. Executives loved the promise of control.

Despite the pain, Siebel gave companies something they had never seen before: a shared operating reality. Leaders could view national pipeline trends without chasing down individual reps. Renewal cycles had structure. Marketing and sales could argue over the same data instead of arguing over separate spreadsheets. For large companies in the 90s, this felt transformational.

The Fall and the Successor

The same qualities that made Siebel powerful also made it vulnerable. As the cloud era took shape in the early 2000s, companies began questioning why they needed massive on-premise installations that cost millions and required constant maintenance. They started looking for something lighter, faster, and easier to adopt.

Salesforce arrived with a clear message: software should run in the browser, not in a server room. The shift from installed software to cloud applications changed the entire economics of CRM. Siebel Systems could not move quickly enough, and in 2006, it was acquired by Oracle.

In a twist of fate, Siebel Systems ended up right back where Tom Siebel began his career.

The Legacy That Never Went Away

Even though Siebel disappeared as a standalone company, its influence is everywhere. The structure of modern CRMs comes from Siebel’s early ideas: contacts, accounts, opportunities, pipeline stages, forecasting tools, dashboards, and reporting hierarchies. Every rep who updates fields in Salesforce or HubSpot is working inside a framework Siebel pioneered. Every CRO who relies on forecasting reports is using concepts Siebel introduced to the mainstream. Every conflict between reps and managers over documentation has roots in the same early battles.

The CRM that sales teams use today looks cleaner and runs faster, but the logic behind it belongs to the 90s. Siebel wrote the first draft. Salesforce simply built the cloud version. Siebel Systems may be gone, but its blueprint is the backbone of modern selling.

URGENCY TALK TRACKS TO TRY ASAP

Too many deals stall out in limbo.

This guide gives your team 10 high-impact talk tracks designed to create urgency without pressure, using proven psychological triggers like FOMO, scarcity, and loss aversion.

You’ll learn how to navigate slow cycles with competitive framing, apply event-based hooks to accelerate decisions, and equip reps with ready-to-use scripts and rebuttals that keep opportunities moving forward.

Don’t wait for prospects to “think about it.” Give your team the words that close.

Download the Talk Tracks Now

Download for free!

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

Approximately how many cups of coffee do Americans consume per year?

A. 146 billion cups
B. 950 million cups
C. 44 billion cups
D. 1.89 billion cups

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I sell workflow software into mid-market finance teams. Not the most glamorous vertical, but dependable. This prospect was a regional loan servicing firm, and getting them into a live demo had taken three months of nudges and reschedules.

I was midway through a video pitch when the buyer held up a hand and said, “One sec… looks like you just sent me something?” I was confused, so it stopped me in my tracks. I watched his face in silence as he read it. Apparently I had completely forgotten to turn off a scheduled email to him after he had replied and booked the meeting with me. So during the meeting it fired off and asked him if he wanted to “set up time to chat sometime this week.”

He read it and smirked at me. I gave a lazy apology, like it was no big deal, and surprisingly, he was super calm about it.

I ended up still landing the deal and have been working with the guy for almost a year now. But I don't manually schedule email follow-ups anymore just in case.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- December 2025

WORTH A PEEK

How much revenue did you generate this year? This was a question recently posed by a Reddit user, and it’s interesting to see just how much (or how little) reps across the country are bringing in. You can check out the discussion here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I’m in software sales, and one of my peers was recently promoted to a team manager role. I was genuinely happy for him at first. We've always been close—we used to grab lunch and joke around all the time. But overnight, he turned into a different person. Suddenly he’s enforcing rules he never followed, policing our CRM hygiene, and giving me “coaching notes” on calls even though our numbers were basically identical last year.

It’s like he’s trying so hard to prove he deserves the job that he’s overcorrecting. I don’t want to resent him, but it’s getting awkward. Should I call him out privately?

Adjusting in Location Withheld

Dear Adjusting,

Don’t call him out, at least not yet. New managers almost always overcorrect at first. He’s trying to prove he belongs in the role, and that insecurity is bleeding into his behavior. Give him some grace and focus on being the steady one. Keep doing your job well, meet expectations, and treat him the same way you would’ve treated any new boss.

If the dynamic still feels strained after a few weeks, ask for a one-on-one and frame it as wanting to stay aligned, not a critique. He’ll relax once the pressure fades, and your friendship has a better shot of surviving if you don’t make this a showdown. Good luck!

Quiz Answer: A. Americans consume approximately 146 billion cups of coffee every year (You can read the source article here).

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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