Smooth Scaling (podcast summary)

Check out the Smooth Scaling Podcast on Apple and on Spotify

Accelerating sales performance using generative AI with Todd Gracon at Workato

• The best sellers are humble, hungry, intelligent, curious, and coachable.
• Test coachability during the interview process.

Optimizing inbound lead capture and conversion with Todd Gracon at Workato

• In early GTM, you are trying to check for signals. You are not going to get that many of them and you are never share where they are going to come from. Since your number one salesperson is your website, you need to drive people there and respond quickly to any indications of interest.
• On your website, make it easy for people to ask for meetings. Moreover, just show people a calendar so there is no need for back-and-forth via email.
• Set up an automation so that if a prospect misses a meeting, it automatically sends out another calendar invite with, “Sorry we missed you, let me know if this is a better time.”

What effective CSMs have in common; Bobby Brown at MessageBird (Part 2)

• “Progress over Perfection” – If you always try to make something perfect, you are going to get left behind.
• When setting up a new process, start with a spreadsheet before going out and buying a new technology.
• Early in the customer journey, you will not have a ton of data so sentiment is the best way to judge customer health. You can also do “Reverse CSAT” = Surveying CSMs to ask them how they felt a customer interaction went.
• You only get one chance to make a first impression.

Structuring post-sales teams for success with Bobby Brown at MessageBird (Part 1)

• CSMs should have technical aptitude, technical curiosity, and project management skills.

Developing a commercial playbook with Natan Pollack at Mambu (Part 2)

• New AEs should spend as much time as possible learning from SDRs since the latter have the highest quantity of unfiltered conversations with prospects.
• Selected playbook elements:
  • TAM/SAM/SOM
  • Sales process (stages with exit criteria, involved teams, KPIs, etc.)
  • Account segmentation and account tiering/classification
  • Overview of various cross-functional teams (partnership, CS, marketing, etc.)

Bringing a product to market through channel partnerships with Natan Pollack at Mambu (Part 1)

• Partner with service providers such as lawyers and accountants when applicable to your product category. Educating them on the value you provide their clients is much more impactful than financial incentives.
• As a global player, you’ll often find yourself competing against local players who are less expensive and less feature-rich. You must enable your reps with strong talk tracks to justify your price premium, most importantly faster time to value and higher ROI via quicker release cycles, more functionality, better service, etc.
• Internal selling is as important a skill as external selling.

Setting up a channel motion with Hayden Stafford at Seismic (Part 2)

• When you work executive to executive, region to region, account to account with partners, you build trust. You know you’ve hit your stride when your product teams are working closely together.
• Send repeatable professional services work, especially implementation, to partners but have them sub-contract back to your team for complex work which typically happens post-implementation.
• Customer success is there to drive ‘how to use’ best practices; they are not there for service escalations. Failing to control this can lead to exploding costs.

Moving upmarket from SMB to Enterprise with Hayden Stafford at Seismic (Part 1)

• When selling Enterprise deals, Microsoft attaches ‘Fast Track’ engineers who work with the sales team during scoping and through implementation. They exist to ensure implementation ultimately goes smoothly. This provides the product & engineering teams with how the product is sold, bought, and delivered.
• Getting implementation right can cut to time to expansion by 50%. or more.

Identifying opportunities by leveraging product market fit with Simon Chassar at Claroty

• To get the attention of large systems integrator partners:
  • Invest heavily in educating the channel on the market need you serve and on the addressable revenue potential for meeting that need.
  • Bring them business to get the flywheel spinning.
  • Build off-the-shelf services methodologies that your partners can lift & apply
• xVT is the multiplier vendor resources inside their partner ecosystem. For instance 10xVT means channel partners have 10x the number of seller, 10x the number of implementation engineers compared with the vendor.
  • Palo Alto Networks operates at 20xVT and Microsoft at 100xVT.
  • Target 10xVT at the $50M-$100M ARR scale. Target 15xVT from $100M to $200M. Above $200M, strive for 20xVT or higher.
• There is an evolution in going from channel account management to channel sales management. The former just identifies opportunities. The latter both influences opportunities and co-sells with you.
• Hiring partner account managers: Someone who has managed a complex SI from a big vendor in your general space

Accelerating customer time-to-value with Lihod Rachmilevitch at OwnBackup

• OwnBackup launched 2 premium support & success offerings:
  • Premier Success: 24/7 support with 1hr SLA
  • Technical Account Management Services: Provides a decided CS person for strategic accounts
• Accelerating time-to-value with customer success managers who are lower cost than AEs should be a priority from Day 1
• Work to accelerate both time-to-first-value (TTFV) and time-to-value (TTV). For example, in data backup, TTFV is when the first backup is complete. TTV is when the customer has an incident and needs to run its first restore.
• Customers are more willing to pay for premium success when the core product offering is mission critical.
• To improve the likelihood a premium success rollout will flourish,
  • Build the offering as recurring (or re-occuring) revenue
  • Provide AEs with full quota credit for the offering (obviously it helps if the margin is similar to that of the core solution)
  • Make AEs eligible for accelerators in the same way they would for any other multi-product sale
• CSMs must be well-trained in objection handling

Scaling from PLG to SLG with Jake Hofwegan at Contentful

• Most PLG companies eventually have to embrace and SLG motion.
• Marketing air cover – field events, digital events, branding, SEM – is critical when standing up and maintaining an outbound sales motion.
• If you verticalize your sales team, then you should also verticalize your product, and vice-versa.
• If you want to get deep into a large enterprise account, you need the help of a BDR to prospect, invite people to field & digital events, share collateral with active contacts, do account research, and share content triggers with AEs so they can engage.

Retaining customers with a value realization framework with Sean Gilliam at Netskope

• You get reduced to the person you sound like.
• We have three roles:
  • CSMs: Focused on business outcomes/value
  • TAMs: Ensuring technical delivery aligns with success plans
  • Technical Success Manager (TSMs): Focused on the ‘how-to’
• We created our value realization framework to ensure smooth pre- to post-sales handoff. It has 5 core questions:
  • Who are the stakeholders?
  • Why did they buy? What value are they expecting?
  • Why did they buy from us?
  • When are they expecting value?
  • How are they going to measure value?

Managing order, transaction, deal desk flows with Ann Neir at Cockroach Labs (Part 2)

• Your first deal desk hire should have some experience but is more of a generalist. They need to not only focus on pricing, commercials, and deal structure but also be able to work closely with reps as well as taking care of paperwork. Moreover, they must partner with Finance to ensure the end-to-end process to functioning smoothly.
• Err on the side of deal desk rather than AEs to shepherd internal contract approvals.
• When you have agreed on a new exception, build that into your CPQ at the very least for the account and often as either a standard term or standard exception.
• ‘Consumerize’ your contracts to be as buyer-friendly as possible to lower barriers to entry.
• Every aspect of the customer experience must be delightful, including contracting.

Understanding and optimizing your funnel with Ann Neir at Cockroach Labs (Part 1)

• Revenue organizations can hit their number via 4 levers:
  • higher ASP
  • shorter sales cycle
  • high win rate
  • more opportunities (top of funnel)
• To have predictability in your business, you need to understand the health of your funnel at every stage. You cannot do that unless you have robust KPIs and reporting. Get as granular as possible as early as possible.
• Each company needs to test whether a PLG sign up is an MQL or simply an initial signal. If the latter, determine and document what it takes to convert free users to qualified leads.
• As obvious as it sounds, one must know and codify what it takes to get prospects from one stage to the next.

Using customer signals for quick wins with Jennifer Chow

• Trigger expansion campaigns for accounts over a certain usage threshold. Build a playbook to execute these campaigns, train AEs, and hold them accountable.

Adjusting and adapting to challenging economic times with Mark Ebert at 6Sense (Part 2)

• When conversion rates drop, don’t rush to stuff more into the top of the funnel. Injecting lower quality opps will likely make the problem worse. Instead, look first to optimize inefficiencies and/or lack of rigor in your sales process.
• Don’t get into a PoC without having an internal win strategy meeting to get fully aligned on how you are going to win.
• There is no point in going to an evaluation unless you are highly confident you are going to win.
• The likelihood of an account buying is much higher for prior closed lost opps. Periodically, run ‘resurrect the dead’ campaigns, esp. when your lost was to no-decision.
• In win-loss analysis, there is nothing more compelling than conversation snippets of prospects explaining why they did or did not buy.
• Invest in sales process early. That way you have data and consistency to be able to tweak what is not working.
• Don’t overdo it with the number of stages.
• If there is one thing you need to nail in your sales process, it is the definition of what constitutes a qualified opportunity.

Moving downmarket from enterprise to SMB with Mark Ebert at 6Sense (Part 1)

• Going downmarket, requires work on product, pricing & packaging, and support.
• Create an SLA to ensure you work high intent accounts via outbound as vigorously as you work an inbound demo request

Managing Inbound Demand and PLG with Navin Persaud

• To figure out what needs to be fixed in your top-of-funnel, sit in the job of an SDR.
• I’d consider replacing an incumbent vendor if I could do more with less or get to my objective faster. I’m not married to my tech stack; I’m married to the outcomes for the company.
• Build tight links between sales ops and marketing ops to ensure inbound leads flow smoothly.
• Seek wins, not glory.
• If someone has gone the PLG route, they have taken the position that they are not yet ready to speak to a human. They first want to go through the product experience and determine, ‘Is this right for me?’ When reps engage, they should position themselves as guides who help reduce time to value.
• As a buyer, I would always like to have a sales engineer on the phone.
• You can’t get good data if you don’t the right process and tooling in place.

How to train CSMs to provide real customer and business value – Daniel Silverstein (Part 2)

• You are doing it right as a CSM if when you get off of a call with a customer, they know something new that they need to know about using your platform.
• We use a marketing automation tool for general communication but we leverage a customer success tool for CSMs to directly engage clients based on trigger events
• Up-market, beware of using too much automation. The level automation depends on the segment you are in.
• We have hard-coded all of our renewal outreach into our marketing automation tool.
• Our enterprise team starts renewal discussions 90 days in advance.
• In post-sale, AI will initially have the most impact on support ticket deflection. However, AI is less likely to help with complex, contextual, up-market problems, especially those that require empathy and trust.

Building a high-performing customer success org from scratch – Daniel Silverstein (Part 1)

• With a larger installed based and lower ACV, [Carta] started with scaled customer success from the very beginning.
• In our customer success organization, we have account managers, program managers, and customer success managers.
• (Program managers are a hybrid of CS strategy/ops & customer marketing/communications.)
• Design your customer success organization for where your clients are in their lifecycle. Our SMB team is largely focused on product education, our mid-market team on upsell, cross-sell, & renewal, and the enterprise team on higher-touch customer success.
• In a non-daily use product, it is harder to use traditional SaaS metrics like daily active users.
• I’d rather hire a CSM who brings a different type of customer problem solving to the team than a person who has solved the problem the same way 1,000 times.
• We teach CSMs a ‘reverse discovery’ problem solving process. This is internal group problem solving 2x per week where we engage on hard customer problems together.

Identifying variables that correlate to win rate with Clay Blanchard (Part 2)

• Model propensity to buy as a single score to adjust your TAM by account into bookings potential. We found several that mattered, including: sector/industry; user growth; tech spend on related products.
• Eventually, companies start to care more about expansion than new business. At that point, you should size the customer lifetime value (LTV). You need years of customer data to determine this accurately.
• There are often inflection point with customers where they buy then flatline with slow growth. Once they reach some critical mass, they accelerate. It is very powerful if you can figure out where that sits. Often you can measure this with user penetration.
• Refresh your TAM once a year
• You need to learn from reps what signals they use to flag good accounts. Then, source that data, add to your models, and make it visible to all reps.

Building your TAM model with Clay Blanchard (Part 1)

• As you scale your field sales organization, especially beyond 100 sellers, you need to evolve your TAM model from directionally correct to more precise in order to inform your segmentation and territory assignment.
• For most SaaS businesses, building a TAM model based on user data is going to give you the most accurate view and also allow you to cut data in a variety of ways.
• Base your target market on target user job titles
• TAM should be aspirational- it is the revenue you would generate if you sold everything you have to every potential user.
• Segment first on size, sector/industry, and geography. To get more sophisticated, layer on high/low growth.
• Not every dollar of TAM is created equal. Layer on propensity to purchase. When selling software, high growth tech companies are typically more likely to buy compared to traditional manufacturers.
• Expose the account-level TAM to reps to help them prioritize their accounts.

Inspire, Coach, and Empower Your Reps with Laura Fu at Kong

• Inspire your reps with the best ‘field stories’ of how their peers were able to win customers. We do this every Monday, in a live 30-min call.
• We ran the ‘Great Pipeline Generation” race for two quarters. We sent a stack rank update every Sunday. This more than doubled pipeline per rep from a year ago.
• ‘Fresh pipeline’ is pipeline (a) created in the last 90 days, (b) forecast to close within the next 6 months, and (c) is in our evaluate stage (post discovery) or better.
• If I could only run one enablement session, I’d do it on Champion Building.
• To ensure a prospect is YOUR champion not just a champion, ask:
  • Are they the one building [or actively contributing to] meeting agendas?
  • Are they owning the EB meeting and framing your solution as the recommended choice?
  • Are they the one building the business case?
  • Are they the one pushing to make sure you speak with the right people?
• The exit criteria for each stage of your sales process must be based on customer verifiable outcomes
• The elements of MEDDPICC start as hypotheses and then get more robust along the way.
• The “E” in MEDDPICC is not only about the economic buyer who signs, but also about everyone else who needs to say yes as well.

Learning from sales ops in different business models with Michaela Downs at Benchling (part 2)

• Leverage a deal desk to offload reps from having to work with legal and finance.
• The sooner you can align sales, success, & marketing under a single leader, the better. Share targets & projects across the team.
• Help reps see the path to attaining quota given their assigned territory. Share not only what they need to do, but also what the company will do to help them.

Creating renewal processes that support 10x growth and 150% net retention with Michaela Downs at Benchling (part 1)

• Leverage CRM automation to automatically generate renewal opportunities
• Your first revops hire should have both CRM admin skills as well as strategic problem solving skills.
• When your reps sign mid-contract expansion deals, ensure these flow through smoothly to your renewal opportunities.
• The sooner you can get your contracting workflows off of Google Doc and onto a tool the better so that you can identify and fix common issues.

Revenue operational effectiveness with Alana Ballon at Wiz (part 2)

• In RevOps, we maintain and syndicate a strategy document that outlines what we are doing and what we are not doing. Though we always want to say ‘yes’ to new ideas, we go back to the document to govern our decision.
• We update our 12-month plan every quarter.
• In re-segmenting, look at how revenue is distributed as well as factors that reflect deal complexity like required resources, win rate, and sales cycle.
• Segmentation is very much about how you align resources to groups of customers and prospects.
• Data is not as good as a compass or a map. It is like a tide. It can guide you, but it can’t be the be all and end all.
• Re-segmenting is a seismic shift – if possible, limit this to at most once a year.
• When standing up a RevOps function, the 3 top things to get right are: compensation, pipeline hygiene, forecasting.

Scaling from one to three cloud platforms with Alana Ballon at Wiz (part 1)

• You are much more likely to get attention from the cloud marketplace providers (AWS, GCP, and Azure) when you have a high ASP.
• To keep incentives clean, retire the same quota amount for reps whether customers buy direct or via cloud marketplaces.
• While contract modifications are easy for customers to execute on cloud marketplaces, they do require complex tools to process on your backend finance and compensation systems.

Aligning customer operations for scale with Laurie Barlev

• When evolving your product from one SaaS platform to another, invest heavily in customer success to support change.
• People who get promoted from customer service to customer success need training on how to move from being reactive on functionality to proactive on value realization.
• Segment your customer success organization based on what is required to serve different types of clients.
• The more complex your software, typically the lower the ARR:CSM ratio.
• Some tips for moving existing customers to new CSMs
  • Group accounts so that you minimize the from-to CSM pairs
  • If the CS director (first line manager) is not changing, then let the customer know they have that continuity.
  • Switch accounts after the renewal

Ownership of revenue between CS and Sales with Eran Aloni at Gong (part 2)

• As we went up market, we separated commercial account management from non-commercial customer success
• QBRs are focused on adoption and tactical initiatives whereas EBRs are focused on value delivers and opportunities to expand the account
• EBRs may involve the AE, CSM, peer execs, PS, partners, value engineering, and product management
• Align books between AEs and CSMs to they can build a stronger partnership
• Don’t switch accounts unless you absolutely have to. Keeping accounts for longer periods has huge benefits.
• Concentrate accounts with similar models with the same CSM.
• Though not written down, our #1 guiding principle is ‘creating raving fans’

Launching a self-service upsell engine with Eran Aloni at Gong (part 1)

• Self-service expansion is critical in the situation where you have many clients who need small upgrades (adding 1 or 2 seats)
• We put a cap on the number of incremental seats a customer can buy online. Over that threshold, we want reps involved since there are likely bigger expansion & value creation opportunities.
• We made sure that reps get the same quota credit whether customer expand via the rep or self-service.
• Truly being customer first is not just words; it means you optimize for the customer when you are faced with difficult decisions

Making your first sales hire with Marcus Holm at Forter

• Your first sales hire should:
  • still be a hands-on player-coach
  • mid-career with strong AE experience and some management experience
  • enough technical aptitude to learn your products
  • enough business acumen to engage with economic buyers and be a strong public voice
• Salespeople will pull in founders as ‘uber solutions consultants’ at every chance; eventually, you need to put some gates in place to ensure:
  • it is the right size opportunity
  • the opp is sufficiently qualified
  • you have the right prospect stakeholders involved
• The AE owns the meeting then pulls others into the meeting as needed. The AE must close the meeting and ‘project manage’ any follow ups.