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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

• Spekit — just-in-time enablement platform; surfaces content, talk tracks, and coaching inside Salesforce, Slack, and other tools
• Salesforce — CRM; "if it's not in Salesforce, it doesn't exist"
• Slack — mentioned as an integration point for Spekit
• 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

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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

• Wisetack
• Aligned - mutual action plans built into the buyer-seller workspace
• Datadog - referenced as Juan's previous AE role
• Salesforce - CRM referenced throughout for MEDDIC and pipeline hygiene
• MEDDIC and MEDDPICC - qualification frameworks referenced in the CRM-hygiene discussion
• Custom sales GPT - Juan's internal AI agent trained on competitors and process for pre-call prep
• Mutual Action Plans (MAPs) - referenced as the discipline both Meredith and Juan double down on

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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

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Meredith Chandler, Head of Sales at Aligned, sits down with Sam Barry, SVP of Sales at Braintrust Growth, to dig into why that happens and what actually changes seller behavior under pressure. Sam's framework, NeuroSelling®, doesn't start with an acronym and work backward. It starts with how the brain processes trust and makes decisions, then builds the communication structure from there.

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This conversation covers what that means in practice: how to open a call with real trust-building instead of rapport theater, why most reps are only doing 50% of the trust work required, and how to use pain quantification to move a stalled deal without a single manipulative tactic.

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👤 Guest Bio

Sam Barry is SVP of Sales at Braintrust Growth, a neuroscience-based sales training and communication consulting firm founded in 2009 and headquartered in Mason, Ohio. Braintrust has been named a Top 20 Sales Training Company by Selling Power every year since 2022. Sam brings over a decade of sales leadership experience, with prior roles including Regional VP of Sales at Richardson Sales Performance and Director of Sales at DecisionWise. He studied human psychology and has spent his career applying those principles inside enterprise sales organizations.

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📌 What We Cover

• Why the brain defaults to features and benefits under pressure, and why adding a new methodology doesn't fix it
• The difference between personal trust and professional trust, and why being strong at only one of them is still failing
• How to open a first call with a point of view that builds credibility before you say anything about your product
• Why rapport-building tactics like commenting on someone's background actually erode trust with senior buyers
• How to quantify pain at multiple levels so a dollar figure becomes the anchor before you ever discuss price
• Why the anchor you set controls the comparison a buyer makes, and how that plays out in pricing and negotiation
• The cortisol-to-dopamine sequence: how naming a financial cost to inaction generates urgency, and how presenting your solution then shifts the emotional state
• What sellers miss when they hear a problem and run with it before truly quantifying what that problem costs

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🔗 Resources Mentioned

• Aligned — AI deal workspace for multi-stakeholder enterprise deals
• Braintrust Growth — NeuroSelling®, NeuroCoaching®, and NeuroServing® programs for enterprise teams
• MEDDIC / MEDDPICC / BANT — sales qualification methodologies referenced in conversation

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The conversation moves into how Keegan approaches GTM builds in 2026 vs. 2019, why he invented the PTP framework (Process, Technology, People), what live intent data changes about warm calling, and where AI is creating chaos inside sales orgs that aren't managing it with structure. Aligned sponsors this episode.

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👤 Guest Bio

Keegan Otter is the Software Cowboy: President of WarmLegency and CRO at Warmly, an AI-powered pipeline acceleration platform that identifies and acts on high-intent website visitors in real time. He joined Warmly in May 2023 as the founding revenue leader and has scaled the company from an unfinished product to crossing $8M ARR. Before Warmly, Keegan held sales leadership roles at Outreach.io, Sendlane, and Postscript, and was recognized by Outreach co-founder Manny Medina as one of the top SDRs on the floor.

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📌 What We Cover

• Why seeing who's on your website and knowing they're ready to buy are two completely different things, and what to do with the difference
• How Warmly killed every direct CTA in their outbound email, replaced them with educational content, and watched click rates go from 2% to 14-18%
• Live intent vs. lagging intent: the grocery store analogy that explains why timing changes everything about warm calling
• The PTP framework (Process, Technology, People) and why building in the wrong order costs you headcount you didn't need to hire
• What Keegan does first when dropped into a company that's still running pure cold outbound in 2026
• Why AI projects inside your sales org need a PM, dedicated timeslots, and the 10% project rule
• The outreach tactics that actually earned meetings (a personalized putting green) and the ones Keegan wants to see die (Venmo payments, unannounced calendar invites)
• How Keegan applies the same GTM framework to his bootstrapped window screen business in Phoenix

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🔗 Resources Mentioned

• Warmly - AI pipeline acceleration platform, Keegan's company
• Aligned - Episode sponsor; AI deal workspace for enterprise sales
• Outreach.io - Sales engagement platform; where Keegan started as an SDR
• Sendlane - Email and SMS marketing platform; prior role
• Postscript - SMS marketing platform; prior role
• Forrester / Topo - Research cited on buyer self-education before demo
• Gong - Revenue intelligence platform; referenced for the general's tent analogy
• Qualtrics - Experience management; prior company of the Gong VP referenced
• HubSpot - CRM; referenced for lifecycle stage logic in AI automation discussion
• Apollo / Outreach / Instantly - Sales engagement and sequencing tools mentioned
• RB2B, Bombora, Demandbase, Clearbit, LiveIntent - Intent data providers integrated in Warmly's platform
• Claude / Claude Code - Referenced in discussion on AI enablement guardrails
• Scott Leese - B2B sales leader and consultant; referenced for applying process-first thinking to a landscaping business

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Michael has been leading procurement teams at enterprise tech companies for over 10 years. He challenges the assumption that procurement is the adversary in a deal and makes the case that sellers have largely created that dynamic by arriving late and leaving procurement with nothing to do but negotiate on price.

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If you're navigating a complex deal where procurement is in the picture, or trying to build a process that stops stalling in the final stage, this conversation will change how you approach it. Brought to you by Aligned.

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👤 Guest Bio

Michael Shields is VP of Procurement at Tropic, an intelligent spend management platform trusted by 500+ companies to bring visibility and control to their software spend. He built the procurement function at Qualtrics from scratch, has led procurement organizations at multiple enterprise tech companies, and is an adjunct professor at BYU in operations and supply chain. He speaks at SKOs and regularly coaches sellers on how buying works from the other side of the table.

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📌 What We Cover

• Why procurement's top pain point with sellers isn't price pressure but being looped in too late, after the only lever left is commercial negotiation
• How to qualify what kind of procurement person you're actually dealing with, from strategic partner to purchasing checkbox, and why that changes your approach
• The three questions procurement asks before price ever comes up: does this tie to a business result, why is this prioritized over the other hundred projects, and why now
• Why every concession you give without a condition trains procurement to push harder next cycle, and the difference between flexibility and optionality
• What ABCD (Always Be Constantly Discovering) looks like in a multi-stakeholder deal, and why treating discovery as a phase instead of a continuous motion puts your deal at risk
• Why champions fail in internal approval rooms when they can't answer "why this vendor," "why this problem," or "why now," and what sellers need to give them instead of a pitch deck
• How procurement's land-and-expand goal is structurally more aligned with sales than most sellers realize, and what it takes to become a supplier they want to grow

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🔗 Resources Mentioned

• Aligned - AI deal workspace for enterprise sales; show sponsor. Build your first room free.
• ABCD (Always Be Constantly Discovering) - Michael Shields' framework for treating discovery as a continuous motion rather than a deal phase

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Meredith Chandler sits down with Morgan Shelly Erazo, Founding Head of Sales at Revenue Vessel, to break down how Morgan closed a $1M+ deal in the SMB segment at Deel, in under a quarter, on a closed-lost opportunity that came back inbound. They cover what created that deal's velocity, how prep and honest expectation-setting moved stakeholders fast, and why LinkedIn connections are one of the most underused tools in any active deal.

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Morgan also shares what becoming a buyer for the first time taught her about how bad most outreach actually is, and how she's building her team at Revenue Vessel around the same principles that made her one of the most recognized SMB closers on LinkedIn.

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👤 Guest Bio

Morgan Shelly Erazo is the Founding Head of Sales at Revenue Vessel, an early-stage logistics sales intelligence platform that gives freight forwarders, customs brokers, and 3PLs comprehensive import data across air, ocean, and cross-border shipments. Before joining Revenue Vessel full-time, she spent 4.5 years at Deel as a Senior Account Executive, where she closed a $1M+ deal in the SMB segment and ranked among the top sales performers in North America. She was named to the 100 Powerful Women in Sales '25 list.

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📌 What We Cover

• How a PE acquisition and new stakeholder hires turned a closed-lost opportunity into a $1M+ deal that closed in a single quarter
• Why new stakeholders entering an account are often a buying signal, not a reset, and how to approach them differently
• How Morgan used an Aligned deal room as a direct differentiator: the key stakeholder cited it as part of the decision-making criteria
• Why brutal honesty with buyers, including delaying her own onboarding timeline, built the trust that accelerated the close
• The pre/post call prep structure that turns a 30-minute meeting into actual deal momentum, and why blocking internal debrief time immediately after calls is a top-1% behavior
• How to use AI for account research without letting it replace genuine curiosity about the buyer's business
• What Morgan now sees as a buyer: why most outbound is unreadable, what gets a response from a sales leader, and why fifth-grade language outperforms jargon every time
• Why connecting with every stakeholder on LinkedIn at the start of an evaluation is one of the most underrated deal moves in the book, and how it creates a live feed of buying signals throughout the cycle

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🔗 Resources Mentioned

• Aligned — AI deal workspace for multi-stakeholder enterprise deals
• Revenue Vessel — logistics sales intelligence platform
• Morgan Shelly Erazo on LinkedIn

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📌 What We Cover

• Why multithreading down the org chart matters as much as getting exec access - and what you miss when you skip it
• How Meredith ran a real call recording tool eval at Aligned and what her reps' daily inputs revealed about BTL influence
• The "out of sight, out of mind" executive reality: why your deal is not top of mind for the buyer's leader, and what that means for your BTL strategy
• Four specific plays to build below the line support: sending relevant resources, gamification, asking directly how to help them get it approved, and echoing day-to-day language over ROI
• Why speaking ROI to a BTL signals you don't understand their world - and what to say instead
• How keeping BTLs looped in between calls surfaces critical deal intelligence, including procurement involvement you wouldn't otherwise know about
• Why your BTL is likely the one who walks you up the chain - and what it costs you if that relationship is weak

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🔗 Resources Mentioned

• Aligned - AI deal workspace for multi-stakeholder enterprise deals. Build your first room free.

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To navigate non-linear buying cycles, you have to run parallel conversations. This requires meeting with stakeholders individually while actively building group consensus. You cannot talk to a sales leader the same way you talk to marketing, RevOps, or finance. You have to tailor your outreach.

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Meredith shares real examples of multithreading done well and multithreading done poorly. You will learn how to send targeted agendas, write tailored email recaps, and warm up key players before a meeting ever happens. If you want to stop chasing a single person who might never show your tool to anyone else, this strategy is mandatory.

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What We Cover

1. Why multithreading requires one-on-one or small group meetings to build individual relationships.
2. How to tailor your interactions to what matters distinctly to sales, marketing, RevOps, and finance leaders.
3. What to do when stakeholders cannot attend every single group call.
4. Sending separate agendas ahead of time so you can focus strictly on delivering value during the meeting.
5. How to write recap emails that highlight outstanding questions for both the large group and specific individuals.
6. The danger of looping senior leaders into highly technical communication threads without setting the stage.
7. Why keeping an executive up to speed without asking for anything makes them naturally curious and more prone to engage.

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Resources Mentioned

1. Aligned: Build your first AI deal workspace for free at alignedapp.com.

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Meredith explains how to tell the difference between a real champion and a helpful ally. Sellers often suffer from "happy ears" when someone shows initial excitement. But if that person does not know the internal buying process or lacks influence, your deal will stall. You need a stakeholder who can actually show you how to buy.

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This solo episode details the criteria every champion must meet: power, motivation, and personal gain. Meredith also shares a recent story about a large deal that slipped because the sole champion left the company. You will learn why multi-threading from the very first call is critical to surviving internal transitions.

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What We Cover

1. The exact difference between a true deal champion and a supportive ally.
2. How to pressure test a prospect's excitement to confirm actual purchasing power.
3. The specific traits every champion must have: power, influence, motivation, and personal gain.
4. Why your internal sponsor needs a direct tie to their core KPIs to push a deal forward.
5. How personal goals like leaving work on time drive urgent purchasing decisions.
6. The danger of single-threading and why win rates jump 30% when engaging four or more stakeholders.

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Resources Mentioned

1. Aligned: The AI deal workspace to handle complex multi-stakeholder deals. Build your first room for free at alignedapp.com.
2. Playbooks and Guides: Access complex sales tips via the link in the podcast description.

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Meredith breaks down why early executive involvement is critical for enterprise deal execution. She explains how to get your name on an executive's radar without flooding their inbox with requests for 20 minutes of their time. The secret is sending updates with absolutely zero asks.

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Meredith shares a real evaluation story where early executive outreach revealed hidden success criteria. Discovering those different priorities early saved a month of selling to the wrong use case. Applying these tactics keeps your stakeholders aligned and separates you from competing vendors.

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What We Cover

1. Why the fear of going over a champion's head is an urban myth that slows down sales.
2. How to loop executives in early using group communications or individual updates.
3. Writing zero-ask outreach to keep leaders informed without requesting a meeting.
4. Using LinkedIn to proactively align stakeholders before formal introductions.
5. How discovering different executive success criteria early can shave weeks off your sales cycle.
6. Setting yourself apart from competitors by proactively managing the evaluation.

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Resources Mentioned

1. Aligned: The AI deal workspace is built to handle complexity in enterprise sales. Build your first room for free at alignedup.com.