Being stuck

[blackswan]

I am currently stuck.

My biggest deal for the quarter has been pushed to the end of the year, and my biggest customers, who I have invested a lot of time in and was hoping to upsell this quarter, have other priorities right now.

If I give it my all this quarter, I might be able to hit 80% quota, but then I need everything to go right and I need a massive hockey stick at the end.

On top of that, my success is extremely dependent on external circumstances and I feel externally determined.
I’m currently in a hybrid role where I have to do account management and net new business. But the reality is that I primarily do account management since the majority of the sales in my team comes from existing customers.
The second big bucket are inbound leads, which make up 50% of our closed won opportunities. In addition, our inbound process is rigged. I know there are AEs who have a special arrangement with SDRs to get leads routed to them. To ensure that I don’t get ripped off, I have taken initial steps and will be monitoring this.
If you work for a large company, in almost all cases, being well positioned internally is just as important as your sales skills.

Okay, enough whining.

What’s my plan?

1. Focus on the most important deals: full focus on the big opportunities and fast execution of transactional deals to keep the focus.

2. Fanatical outbounding: it will be hard to turn this quarter around, but the fiscal year has just started, now the seeds are being planted for the fruits I will reap throughout the year. Next week I have 9 customer meetings, the goal is to make it 10 and keep the traction going.

3. Inbound control: I will not get ripped off and will take total responsibility for my territory.

4. Leverage the channel. I plan to involve partners more and divide my book of business into Tier 1, Tier 2, Tier 3 and Tier 4 accounts. I will hand off Tier 4 and some Tier 3 accounts to the partner.

5. Positive mindset: I will influence the things I can influence. This is often more than we think. If nothing is really moving forward, just skip two or three levels and shoot people a DM. It’s a job. If I get punished for it, then it’s a company I don’t want to work for.

What do you think? Have you been in a similar situation and what did you do?

[blackswan]

Yesterday was the last day of the quarter, and I managed to turn things around again and will end up at just over 90%.

I actually wanted to write an interim update, but because it wasn’t clear until the last second where I would end up, I had total imposter syndrome.

Because nothing went according to plan this quarter (February–April), absolutely nothing.

In the original message from March, I wrote that my biggest deal had been pushed back.

At the end of March/beginning of April, it turned out that not only this deal was being postponed, but two others as well.

That’s why I had imposter syndrome. I felt like I had no control over my key deals because all the tried-and-tested methods weren’t working. My coach blocked me from the executive buyer and preferred to present his own results instead of taking me to the decision meeting (which was pretty dumb and ended up being the biggest roadblock in the deal), and with another customer, procurement was an absolute show stopper.

What would I do differently?

To be honest, I would have prioritised other opportunities. I have been in talks with the one customer for about 6-7 months and we have conducted two trials. It is just as important to disqualify opportunities as it is to qualify them. Diagnosis: chronic indecision. No happy ears.

The other opportunity with procurement was just as shaky. I had no champion in the deal and no hard pain.

At the same time, I have to say that I didn’t have any other opportunities for a long time. What I mean by that is that all the MEDDICC Playbook knowledge is all well and good, especially when things are going great, but when nothing seems to be working and there are no alternatives, you have to take risks.

How did I manage to turn things around?

I brought forward two large deals from Q2. Both accounts were due for renewal and I had already done months of groundwork.

This relationship of trust gave me the opportunity to present attractive offers that were limited to April.

That sounds like a no-brainer and totally easy, but honestly, it didn’t work with all customers I tried it with.

In practice, this meant that every week I calculated exactly which deals I still needed and how much they had to be worth in order to reach my quota.

And then it was a hell of a grind to find customers who were willing to take the next step and set them up for success.

My lessons learned:

1. Focus on the right opportunities and qualify out

2. Sometimes you just don’t have any luck. For me, that can be a few weeks, but I’ve also seen good sellers who had several quarters that simply went badly.

3. Never give up. If you do a lot, you increase your chances of finding opportunities, and then you have to seize them.

4. Trust creates revenue.

[blackswan]

I could honestly keep this thread going forever because my own personal soap opera just won’t end.

This quarter, I have two key renewals from my Tier 1 customers. In both cases, my champion left the company just a few weeks before the renewal date.

Now I’m dealing directly with Procurement. They’re just doing their job, of course. But the way they try to push the price down sometimes feels… off. In one case, they even used a lie to gain leverage. And while I know that’s not personal, it still hits hard.

I once heard someone say:

“The best way to negotiate is to make the next negotiation easier.”

That’s exactly my philosophy. Good negotiations lead to long-term partnerships, not winners and losers.

I’ve never been a fan of the “Never Split the Difference” mindset, based on the popular book by former FBI negotiator Chris Voss.

For those who haven’t read it:
The core idea is that you should never compromise in negotiations. Instead, you should use tactical empathy, calibrated questions, and psychological levers to guide the other person toward the outcome you want, without giving ground.

Now, I get it.
These methods may work in situations like hostage negotiations, where there’s no room for mutual benefit, just clear stakes and clear outcomes.
But in a business context, especially in Tech Sales, I believe this mindset is not just unhelpful - it can be dangerous.

Business relationships thrive on trust, transparency, and mutual respect.
I don’t want to “win” a negotiation by outsmarting the other person. I want both sides to walk away feeling like it was a fair, productive conversation that made the next conversation easier, not harder.

That’s why I don’t push my pricing aggressively and I expect the same in return.
If a customer starts the negotiation with half-truths or dirty tactics, just to push down the price, I seriously question whether it’s the kind of partnership I want to invest in long-term.

Anyway, the soap opera didn’t end there.
I also received another rejection last week from a key deal. They said they got no budget approved this year.

Still, I made a promise to myself: I won’t give up.
If I pulled it off last quarter, maybe I can do it again.

But I’ll be honest with you:
It’s incredibly frustrating to give it your all and still land at 80–90%.

What stings the most is when you see colleagues working 6 hours a day, with three Tier 1 customers who expand every quarter, while you’re grinding through every inch just to keep pace.

But complaining doesn’t help.
Life isn’t fair. And neither is sales.

[Coon]

I’ve been thinking a lot lately about how much success in sales depends on factors that are outside of your control.

I recently joined a new company and was given a small account patch – around 40 to 50 accounts. Most of them have likely never talked to us. That means your success can be heavily tied to whether just one or two of them decide to buy. If they do, you hit your quota fast. If they don’t, it gets tough – especially with long sales cycles and strong competition, since all of these accounts already have something in place.

What makes it even more challenging: my outreach is naturally limited. I simply can’t make 30 cold calls a day because I don’t have the volume of the right contacts within this patch.

But I really like your plan and will definitly take something from it with me

[blackswan]

Thanks so much for sharing this, it’s exactly why I started the forum.

Because there are so many reps out there in similar setups, and the standard Sales Guru advice like “just do more” doesn’t always work, especially when your patch is limited and product-market-fit isn’t a given.

If I were in your shoes, I’d probably try:
– Investing in a lead database like Lusha to get more threads per account (if your company has none)
– Building a simple account tiering model: who has urgency, who just looks nice on paper
– Multithreading every single account, even if it’s just 2–3 people per org
– But also: drawing a clear line.
If there’s zero traction after 6+ months, and you’re working 40–50 hours with no progress, then it’s not on you.

Sales can feel like you’re sprinting uphill with a backpack full of bricks.
You need to know when to lean in and when to stop climbing the wrong mountain.

Glad you’re here.