Complex Sales: Decoded

Most sellers have never made a big software purchase. Meredith Chandler hadn't either before she stepped into leadership. Now that she's been involved in dozens of big-ticket software purchases, the way she coaches sellers has completely changed.

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Meredith walks through the three things an AE needs to unlearn to consistently win big deals. First, stop asking whether your buyer has budget. Companies move money toward whatever becomes urgent enough, so the real question is whether the problem you solve is important enough to move budget around for. Second, the person who feels the pain usually can't actually spend the money, and that money travels a very specific path to get released. Third, "we don't have budget" almost never means the money doesn't exist.

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She's been on the side that approves the budget time and time again, and she says that exact sentence herself all the time. What it usually means is that this isn't a priority right now, or there's no bandwidth. That's not a closed door for a strong rep willing to put in the work. Brought to you by Aligned.

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📌 What We Cover

• Why there's never budget and yet there's always budget, and what the leaky roof teaches you about where money actually sits
• Why underperformers believe budget is a fixed pot of money sitting around in an account somewhere, and why there is no fixed pot
• What to ask instead of "Do you have budget?": what they funded recently, and why, so you learn what urgent enough looks like at that specific company
• Putting the cost of their problem into real numbers so it can outrank the other things competing for the same dollars
• Why pouring everything into one excited champion leaves deals dragging for months before they slowly disappear
• The question that surfaces the approval path: "Walk me through how something like this typically gets approved"
• How to find which budget the money comes out of and who owns it, and why that's the person to get involved early
• Why offering a discount is the worst response to "we don't have budget," and what building a business case to earn the budget does instead

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🔗 Resources

• Aligned, the AI deal workspace built to develop champions with mutual action plans and keep deals from stalling out. Build your first room for free.

Most sellers lose the deal in a room they were never invited to. Your champion is excited, but unless they control the budget, they're walking into a leadership meeting where 10 problems are competing for a budget that covers three. What they can say without you there decides the outcome.

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Meredith Chandler, Head of Sales at Aligned, breaks down the four pillars of a business case that makes your champion sound like the smartest person in that room. She covers writing the current challenges in the buyer's own words instead of translating them into sales language, putting a number on the pain, extending that number forward in time until it becomes unignorable, and choosing a case study your buyer can actually see themselves in. She closes on the section most sellers skip: predicting the objections your champion will face and answering them before anyone gets to ask.

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📌 What We Cover

• Why top reps aren't better at selling, they're better at enabling buyers to sell internally when they can't be in the room
• Pillar one: describing the pain in your buyer's language, using their KPIs and their priorities, in one or two sharp sentences
• Why "reps are wasting hours rebuilding the same proposal" belongs in your document as they said it, not translated into "inefficiencies in the sales workflow"
• Putting a number on the pain: 12 AEs losing five hours a week becomes roughly 3,000 selling hours per year
• Pillar two: extending the number forward in time and converting it into dollars, because 3,000 selling hours is the output of one extra rep carrying a million-dollar quota
• Pillar three: the time to value formula, a company like theirs, in this timeframe, hit this metric they care about, in the same unit as their cost of inaction
• Why naming OpenAI as your customer example backfires when you're selling to a Series A startup
• Pillar four: preempting the "Yeah, but" on budget, security, integration risk, adoption, other initiatives, and bandwidth, and working with your champion to name which ones will actually come up

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🔗 Resources Mentioned

• Free business case template (link in the episode description)
• Aligned, the AI deal workspace for large multi-stakeholder deals

Deals are more competitive than ever, and when every vendor is good enough, execution becomes your differentiator. A better run sales process can beat a better product any day of the week.

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Meredith Chandler, Head of Sales at Aligned, walks through four questions to start asking much earlier in every deal. The first one sounds obvious, but it's the one she sees reps avoid the most: who else are you evaluating?

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The problem isn't that sellers don't know competition exists. Asking directly seems more like an interrogation, so the buyer says no just to move on. Meredith reframes each question so the buyer answers honestly, then covers what to do with the answer. Why are they evaluating those other tools to begin with? Where do you actually rank, and what is that competitor doing better right now?

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The final question is the one that changes the deal: how will you ultimately decide? That answer turns your buyer into your coach on how to navigate the deal across the finish line. It also becomes the mutual in your mutual action plan.

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📌 What We Cover

• Why you should always assume you're in a competitive deal, and why hot leads don't protect you when every vendor is good enough
• The assumptive phrasing that normalizes competitors: most buyers I talk to looking at a tool like this are also evaluating one or two others, so who else is on your list?
• What "there's nobody else" usually means, which is that they're comparing you to the status quo or they haven't done the work yet
• The two moves most sellers make at that point, and why taking it at face value leaves valuable information on the table
• Why "why them?" matters more than knowing which tools are on the list: a former company, a colleague's recommendation, a CEO nudge, shared investors
• How to find out where you actually rank without asking point blank, by asking where the perceived gaps are
• Why the competitor strength a buyer names is the real objection that needs to be overcome
• How "how will you ultimately decide?" surfaces what to prioritize: team feedback, user feedback, price, terms, rollout and implementation

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🔗 Resources Mentioned

• Aligned, the AI deal workspace for large multi-stakeholder deals. Build your first room for free.
• Mutual action plans, plus the follow-up video with a step-by-step guide to building one
• A future episode on selling against the status quo

You got off a great demo. Your champion loved it, replied fast, and you assumed there was strong internal alignment. Then two weeks go quiet, and the reply is "a few internal questions came up." You don't know what those questions are, who's asking them, or what your champion will say back. That's how stalled deals become dead deals. In this solo episode of Complex Sales: Decoded, Meredith Chandler breaks down how she trains the team at Aligned to help buyers close their own deals. The through-line: the deal lives in your buyer's activities, not yours, and your job is to equip your champion for the rooms you'll never sit in.

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📌 What We Cover

• Why meetings held with your buyer are the wrong metric to track, and why the deal lives or dies in your buyer's activities.
• The three-to-ten-hours rule: for every hour a buyer spends with you, they spend three to 10 hours internally without you, and you influence all of it through what you hand them before those meetings.
• How to map the buyer's internal approval process instead of your own sales stages, and the exact question to ask your champion to start that map.
• The test for whether your champion is real: "If I weren't able to join the next internal meeting, what would you say?"
• The four assets that move deals when you're not in the room: the problem statement in the buyer's language, a stakeholder-specific FAQ, a one to one-and-a-half-page business case, and a mutual action plan.
• Why the "you're probably thinking" section pre-surfaces objections in your champion's own language before a skeptic raises them.
• Keeping the mutual in mutual action plan by building the timeline around the buyer's internal milestones, not your quarter-end quota.

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🔗 Resources Mentioned

Gal Aga's Linkedin Post

Aligned, the AI deal workspace for closing large multi-stakeholder deals.

Your best rep can have the better product and still lose a 300K deal, not on price, but because nobody got the buying committee aligned on what they were doing. On this episode of Complex Sales: Decoded, Meredith Chandler sits down with Gal Deitsch, co-founder and chief product officer of Aligned, to talk about why buyers don't want to be sold to anymore and what sellers do about it. They get into the operational skills modern sellers need across a dozen stakeholders, the buyer behaviors that reliably signal a deal will close, and the mistake most sellers make when they build a mutual action plan with themselves instead of with the buyer. Gal also reads engagement data from tens of thousands of deals a month, so the signals he describes come straight from what closes and what stalls.

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👤 Guest Bio

Gal Deitsch is co-founder and chief product officer of Aligned. He was a director of sales before he started the company, after watching his top rep lose a major deal because she couldn't keep a 12-stakeholder buying committee aligned. As CPO, he now looks at data across tens of thousands of deals running through Aligned every month.

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📌 What We Cover

• Why a stronger product still loses when nobody keeps the buying committee aligned, and why sellers now need managerial and operational skills, not just a good demo
• What changed in B2B buying: buyers self-educate, talk to their own committee, and run everything through AI before they want a seller
• How to make a deal buyer-centric when you're juggling five, six, seven or more stakeholders
• The buyer behaviors that signal a deal will close: engagement spread across stakeholders, steady champion room time, and a trend that climbs toward the end
• Why disengagement is its own signal, and how "no news" usually means the deal isn't advancing
• What sellers get wrong about the mutual action plan, and how the best reps build it with the buyer and revisit it every meeting
• Why discovery isn't a stage but something woven through the entire cycle

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🔗 Resources Mentioned

• Aligned, the AI deal workspace, including its digital sales room, mutual action plans, and engagement signals
• Mutual action plan (MAP)
• Slack
• Spotify and Apple Podcasts

Most reps build the deal around the people they can see. The champion, the user, the manager who sits in on the calls. The stakeholders who actually decide whether you close, the CFO, the controller, the procurement lead, often sit in the background where you never reach them. Meredith Chandler breaks down how to pull those hidden stakeholders to the forefront before they can kibosh the deal at the final step.

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She covers why running the deal entirely through your champion is a mistake, what happens to your proposal after you send it, and how a shared deal workspace in Aligned shows you everyone who so much as looks at it. If your deals keep stalling late, this one is about seeing the people who were quietly influencing the outcome the whole time.

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📌 What We Cover

• Why running the deal entirely through your champion is risky, and how a single no up the chain can stall everything at signature
• How a champion can mistake one negotiable term for an absolute deal breaker when you actually had room to negotiate
• The two distinct groups of stakeholders in every deal: the ones you see and the ones you don't
• Why it's best practice to get your own access to all of those stakeholders, not just your champion
• What actually happens to your proposal after you send it over email, and why you normally have no idea
• How a shared workspace draws hidden stakeholders, like a forwarding CFO or a budget-checking controller, out of the shadows and into view

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🔗 Resources Mentioned

• Aligned, the AI deal workspace for multi-stakeholder deals
• Get the full, Advanced Multi-Threading Playbook

You've figured out when to reach out to execs, how to reach out, and what to say. But sometimes the fastest way into the C-suite isn't another email from you. It's bringing in your own executive team. In this episode, Meredith Chandler, VP Sales at Aligned, breaks down how to make it effortless for your leaders to open doors, build trust, and keep deals moving at the top of the org. The same idea you use with buyers (relevant context, kept informed every step of the way, not pulled in at the finish line) applies to your internal sales team, too. Exec-to-exec outreach opens doors because execs fast-track fellow execs, and there's an almost automatic layer of trust that comes with it. Meredith walks through when to bring an exec in, exactly what to equip them with, and how to write a note that actually sounds like them.

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📌 What We Cover

• Why exec-to-exec outreach stands out: an exec's inbox is full of AE prospecting and nearly empty of peer outreach, so a note from another leader gets read as already researched and purposeful.
• The three moments to pull an exec in: intros to break into a cold account, continued support after a strong demo, and stalled deals losing momentum.
• Treat your internal exec like a prospect: make it easy to say yes, give no surprises, and agree on timing long before the moment you actually need them.
• Exactly what to hand your exec: a LinkedIn profile, one to two sentences of context, the current challenge, your desired outcome, and a short note written in their voice.
• Why "in their voice" matters, and how to get there with AI: upload an exec's emails, blogs, and LinkedIn posts, build an ongoing memory, and push it to sound more senior.
• The stalled-pricing play: an exec sends a short video offering a direct line to get unstuck, which removes rounds of messenger back and forth.
• The gone-dark play: ask exec to exec for honest feedback on the process so you can learn, even when reviving the deal is unlikely.
• Going higher for must-win logos: looping in the CEO or chief product officer, and refining an AI memory so leadership makes fewer edits over time.

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🔗 Resources Mentioned

• Aligned (the AI deal workspace; build your first room free)
• Get the full, Advanced Multi-Threading playbook

Enterprise sales often stalls on the same two obstacles: a buyer who isn't ready to move yet, and a rep who doesn't know how to handle that gracefully. This episode of Complex Sales: Decoded digs into both. Meredith Chandler sits down with Valerie Avila, Head of International Sales at Justworks, to talk through the specific dynamics of selling a complex product to buyers who don't yet understand the territory, literally and figuratively.

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Valerie has spent nearly 12 years at Justworks, building out domestic expansion and now leading the company's international sales motion. The conversation covers what separates effective objection handling from deal-killing rabbit holes, how real-time coaching is making a comeback through AI, and why "not right now" is one of the most important pieces of data a rep can collect.

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👤 Guest Bio

Valerie Avila is Head of International Sales at Justworks, where she has worked for nearly 12 years. She joined as an Account Executive in 2014 and has held roles across sales management, training, domestic expansion, and revenue development. She founded the Justwomen initiative, a speaker series that brought prominent women executives together to drive growth in the NYC tech community. Before Justworks, Valerie was in business development at SinglePlatform. She holds a BA in Communications and Philosophy from Boston College.

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📌 What We Cover

• Why selling international EOR is a fundamentally different motion from domestic PEO: Justworks becomes the full legal employer abroad, which means buyers are carrying assumptions from US employment law that don't transfer.
• How Justworks unified its domestic and international sales motion under a single AE supported by specialist overlays, and why splitting by product early didn't serve the same customer effectively.
• What just-in-time enablement looks like in practice: Justworks uses Spekit to surface talk tracks, answers, and collateral inside the tools reps already use, without requiring them to break their workflow.
• Why real-time coaching on live calls matters, the old whisper/barge function and how AI is rebuilding that capability for a remote-first sales environment.
• The objection triage framework: before handling any objection, ask whether it is a smoke screen or a real deal breaker, and whether the person raising it is the one who actually drives the decision.
• Why fixating on a small objection, a missing feature, a font, can turn a winnable deal into a mountain the rep built themselves.
• The timing objection unpacked: "it's never a no, it's a no for now." Fiscal year start, benefits renewal, and vendor contract end dates are the moments that matter, and every conversation should go into Salesforce so the follow-up can happen at the right one.
• How to stay relevant between conversations using signals, from LinkedIn activity to company events to building a custom AI agent to monitor buying intent triggers.

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🔗 Resources Mentioned

• Pavilion's AI and Go-To-Market School — operator-led GTM learning program, Valerie is currently enrolled in
• Claude — mentioned as a tool for building custom AI agents to track buying signals
• Aligned — episode sponsor; AI deal workspace for multi-stakeholder enterprise sales

When a buyer says yes after months of pursuit, the rep's instinct is to lock the deal down and stop selling. That's where most enterprise deals quietly crack open. In Episode 10 of Complex Sales: Decoded, Meredith Chandler sits down with Juan Arcila, Sales Manager of Mid-Market Sales at Wisetack, to talk about what it actually takes to move a complex deal forward when you're displacing an incumbent, running against multiple vendors, and selling to a buying committee you'll never fully see. Juan walks through how his team uses AI to come into first calls with a hypothesis instead of a Q&A dance, how to stack rank a buyer's priorities when the deal is "neck and neck," and the year-long pursuit that he almost lost because he got happy ears. The conversation closes on mutual action plans, CRM hygiene as a seller tool, and why arming a champion is the actual sales motion in a complex cycle. This one is for any AE or sales leader sitting on a verbal yes that hasn't held up yet.

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👤 Guest Bio

Juan Arcila is Sales Manager of Mid-Market Sales at Wisetack, the embedded consumer-financing platform for in-person service businesses, where he leads the team selling to merchants in home services, dental, auto, and elective medical. He started his sales career in SDR and AE roles at Wistia before joining Datadog as an Account Executive in the Commercial segment, and he now coaches the Wisetack mid-market AEs through competitive cycles against incumbent lenders.

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📌 What We Cover

• Why the bottleneck in Wisetack's cycle isn't the demo-to-signup conversion, it's the first activation, and what that pattern reveals about adoption inside owner/operator businesses
• The two sales happening inside every competitive cycle: convincing leadership to switch, and convincing the end user to actually log in
• How Juan's team uses a custom GPT to pull a competitive-analysis prep doc before the first call, so reps walk in with a hypothesis instead of running a 10-questions-back-to-back hot seat
• The exact reframe to use when a buyer says it's "neck and neck": go back to discovery, stack rank their priorities, and pressure test which gaps you actually solved
• Why "the team will give us a thumbs up" is a non-answer, and what disqualifying questions to ask before you trust it
• How Juan equips a champion for the rooms he'll never sit in, including pre-loading them with the resources each stakeholder will care about before that next internal meeting
• The Salesforce hygiene shift Juan only understood once he moved into management, and the AI-CRM middle ground his team landed on so reps don't "set it and forget it"
• The year-long deal Juan nearly lost because he got happy ears, and the playbook he runs now to pressure test a verbal yes before procurement and the C-suite ever see it

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🔗 Resources Mentioned

• Aligned - mutual action plans built into the buyer-seller workspace

Multi-threading goes wrong when sellers treat executive sponsors like a closing-mile play, pulling them in at signature when they don't even know your name. This is the fifth episode in the multi-threading series on Complex Sales: Decoded, and host Meredith Chandler breaks down how to engage above the line throughout the deal cycle, not just at the finish line.

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The episode covers when to reach out to execs, what those communications should actually look like, and how to stay visible without becoming the rep execs avoid. Meredith uses a marriage-proposal analogy to make the point: warming someone up over time is what makes the big ask possible. She walks through three rules for above the line outreach, the right reasons to send, and a real-world example of a deal that got killed because the right people weren't in the loop. Brought to you by Aligned.

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📌 What We Cover

• Why pulling in an executive sponsor at signature is the late-stage move that kills deals
• The dating analogy for multi-threading, and why "who the hell are you" is the response you can't afford to get at signature
• Three rules for above the line outreach: short and sweet, outcomes not activities, and "no action needed" as the closer
• Why every above the line touch should provide momentum, not pile on asks
• The right reasons to write an executive: alignment between solution and company goals, POV kickoff or wrap, confirming consensus before pricing
• Why writing to check a CRM box or appease RevOps is the email that gets deleted
• A real example of an internal eval that got killed because the buyer and team weren't multi-threaded

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🔗 Resources Mentioned

• Aligned deal workspace, for moving multi-stakeholder deals out of email threads and developing champions with mutual action plans
• Get the full, Advanced Multi-Threading playbook