Software Sales Tips: How the Best AEs Close More Deals
The software market is noisy, the buyer is educated, and the competition demos every week. Here's how top AEs stand out and win.
Why Software Sales Is Different
The Buyer Has Already Done Their Research
Before you get on a discovery call, your prospect has read G2 reviews, watched competitor demos, and built an internal shortlist. You're not educating them about the category — you're differentiating in a market where everyone claims to do the same thing. Generic pitches lose before they start.
You're Competing With Free Trials and Freemium
Your competitor is giving away a version of their product for free. That changes the stakes of every demo and every follow-up. If your trial doesn't activate fast — if the prospect doesn't experience value within the first week — a free alternative fills the gap and your deal quietly dies.
Multi-Stakeholder Deals Kill Momentum
The person you demo to is rarely the person who signs. IT needs to approve security. Finance wants a business case. The end users need to want it. Multi-threading from day one isn't optional — it's how you stop a six-figure deal from dying at the procurement stage.
10 Software Sales Tips That Fill Your Pipeline
The Problem-First Discovery Call
Most AEs open discovery by asking about current tools or team size. The best ones open with a single question that surfaces pain immediately. Leading with the problem — not the product — changes the entire dynamic of the conversation and makes the prospect sell themselves.
Script
"Before I tell you anything about what we do, I want to make sure this is actually relevant to you. Can I ask — what's the one thing you wish your current solution did better? Not a features list — just the one thing that, if it were fixed, would make your week significantly easier."
The Champion Identification
Your champion is the person who will sell for you when you're not in the room. Without one, you're relying on the economic buyer to understand the problem, the solution, and the ROI — which rarely ends well. Find your internal sponsor early and equip them with everything they need to close the deal internally.
Script
"[Name], before we set up time with your leadership team, I want to understand the landscape. Who else is going to be part of this decision — IT, Finance, anyone in legal? And who would you say is most invested in this problem getting solved?"
The Demo That Leads With Pain
Feature-led demos lose. Outcome-led demos win. The moment you open a demo with a product tour, you've given the prospect permission to evaluate features instead of visualising results. Build every demo around the specific pain surfaced in discovery — and check your assumptions before you start.
Script
"Before I show you anything, let me check I've built this around what actually matters to you. In our last conversation, you mentioned [pain point]. I've structured this around that — but if priorities have shifted, I'd rather adjust now than walk you through the wrong thing."
The Trial Activation Play
Most trials die from inactivity, not dissatisfaction. The prospect signs up, gets a login, intends to explore — and two weeks later the trial has expired and they feel vaguely guilty about it. A day-3 check-in that focuses on a single activation action is the highest-leverage thing you can do after signup.
Script
"Hey [Name] — you signed up a few days ago and I wanted to check in before the trial goes quiet. Have you had a chance to [specific activation action]? That's usually where people start seeing it click. I can walk you through it in 10 minutes if that's easier than figuring it out solo — what does your calendar look like this week?"
The Multi-Stakeholder Email
When a deal involves multiple decision-makers, your champion needs ammunition. A well-crafted 'why change' email — written for the economic buyer, not the user — gives your champion something they can forward without editing. If you make them write it themselves, they won't.
Script
Subject: Re: [Your Company] — context for [Finance/Leadership] Hi [Economic Buyer], [Champion name] asked me to send some context ahead of your conversation. The short version: [Company] is currently [current state / problem]. We work with teams like yours to [specific outcome], typically within [timeframe]. The business case is straightforward: [1-line ROI statement]. Happy to join a 20-minute call to answer any questions directly. [Your name]
The Procurement Navigator
Procurement stalls more software deals than objections do. The rep who treats procurement as a surprise at the end of the cycle loses weeks they can't get back. Getting ahead of it — vendor forms, security questionnaires, MSA templates — is the difference between closing in Q3 and slipping to Q4.
Script
"I want to make sure we don't lose time on the admin side once we're aligned on the commercial decision. Can you walk me through what your procurement process looks like from here? Vendor forms, security review, legal — I'd rather start those in parallel than queue them up after we agree terms."
The Security/Legal Objection
IT and legal are paid to slow things down. That's not obstruction — it's their job. The AEs who handle this well don't wait for the security questionnaire to land in their inbox three days before close. They proactively introduce their own security team, offer to pre-fill questionnaires, and remove the friction before it becomes a blocker.
Script
"Happy to loop in our security team directly — they've been through this process with [type of company] dozens of times and can usually turn a security review around in two to three business days. If you send me the questionnaire, I'll have it back to you before your IT team has a chance to ask for it."
The Competitor Comparison
When a prospect is evaluating three tools, the worst thing you can do is attack the competition. The best thing you can do is surface the specific hesitation they have about choosing you — and address it directly. Most reps avoid this question. The ones who ask it close more.
Script
"Can I ask — you mentioned you're looking at a few options. What's your biggest hesitation between us and [Competitor]? I'd rather know now than have it come up at the contract stage."
The Price Justification
CFOs don't reject software on price — they reject it when the ROI isn't clear. If you haven't quantified the outcome in discovery, price will always feel high. Anchor the value to a number before you ever share a quote — and let them do the maths.
Script
"Before I send over the proposal, I want to make sure the numbers make sense. If we help you [specific outcome from discovery], what's that worth over 12 months? Even a rough number — I want to make sure the ROI story is obvious when this lands on your CFO's desk."
The Stalled Deal Revival
Deals go dark for three reasons: the champion lost internal support, the budget dried up, or something higher-priority took over. A good revival email acknowledges the silence without apology, offers an easy out, and gives them a reason to re-engage — without the whiff of desperation.
Script
Subject: Still on your radar? Hi [Name], It's been a few weeks since we spoke — I don't want to assume this is still a priority if circumstances have changed. If the timing isn't right, just let me know and I'll follow up in Q[next quarter]. If it is still on your radar, I'm happy to pick up where we left off — we've had a few new [relevant customer wins / feature releases] since we last spoke that might be useful context. Either way, worth a quick reply? [Your name]
The Software Sales Conversation Framework
Every software deal moves through five distinct stages. Top AEs own each stage deliberately — they don't rush demos before discovery is done, and they don't pitch pricing before the business case is built.
- 1Discovery— Open with the problem, not the product — surface pain, quantify it, map all stakeholders→
- 2Demo— Build the demo around the specific pain from discovery — outcome-first, feature-second→
- 3Proof / Trial— Drive activation to the one moment that delivers the core outcome — don't let trials go dark→
- 4Business Case— Quantify ROI with the economic buyer, proactively handle security/legal/procurement in parallel→
- 5Close— Agree a mutual action plan with a go-live date — close is a process, not a single conversation
What Top Software AEs Do Differently
Quota attainment in software sales isn't about working harder — it's about executing the right behaviours consistently across every deal in your pipeline.
- ●Run deep discovery before every demo — they never show the product until the problem is quantified
- ●Identify and develop a champion in the first two calls — someone who will sell internally when the AE isn't in the room
- ●Multi-thread from week one — IT, Finance, and the economic buyer are in the conversation before the business case stage
- ●Hold a weekly deal review on every active opportunity — stalled deals get surfaced and actioned, not carried forward quarter after quarter
- ●Send strong written follow-up after every call — a summary email that confirms the pain, the agreed next steps, and the timeline is worth more than any CRM note
Related Resources
Get The Futureproofed Sales Playbook — $47
The complete playbook — frameworks, scripts, and systems for every stage of the sale. Used by 500+ salespeople.
30-day money-back guarantee. Instant download.