Hey friends, I’m Akash!
Software Synthesis analyses the intersection of AI, software and GTM strategy. Join thousands of founders, operators and investors from leading companies for weekly insights.
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Over the last year I’ve had the privilege of interviewing leading operators at some of the most enduring software companies, including Stripe, Figma, Notion, Retool, Databricks, and more.
This blog has always been in the service of founders. So, to finish the year, I decided to combine the lessons from the 13 interviews we did this year across marketing, sales, community, partnerships, customer success and more.
Hopefully this serves as a resource for founders looking to tune any specific elements of their GTM engine. Thank you for all of your support this year!
Marketing
Alex Rodrigues, Head of Product Marketing at Superhuman:
A Product Marketing Manager (PMM) is the best first Marketing hire a young company can make, especially if it's still searching for product-market-fit.Hiring a PMM as your first marketing role is a strategic move. It places marketing at the heart of your business strategy, ensuring it's a data-driven function aligned with your company's growth and customer needs.
In a more sales-led or Product-Led Sales (PLS) business, PMMs might primarily drive demand generation, creating leads and collaborating closely with Sales teams. They develop customer journeys that facilitate swift deal closures, working alongside Sales to empower them with the necessary tools and insights for success.
Revenue acquisition stands as the top priority for PMMs, especially in the current market landscape. PMMs should be owning or influencing revenue that's coming in, and focus on strategies that sustainably increase growth over time rather than just causing temporary spikes. It's also essential to set and monitor objectives further up the funnel, like increasing signups and boosting website traffic.
As an initial marketing hire, a PMM typically reports to a revenue-focused leader – this could be the Head of Sales, Head of Growth, or COO, or alternatively, a product leader role. Regardless of reporting structure, it's essential for the PMM to engage closely with engineering, product, design, and GTM teams, as their work significantly influences these areas
Romain Doutriaux, ex-Pigment and Dataiku
Marketing is fundamentally about telling impactful stories. Under this definition, what falls under marketing's remit becomes clearer. It can be divided into three buckets:
- Product marketing: How do we sell the product, but also how do we influence the product roadmap based on what we're able to sell in the market and ecosystem?
- Awareness/branding: How do we educate our potential buyers? How do we educate a wider audience?
- Lead generation: How do you drive pipeline? How do you ensure there's an impact on the P&L, on the bottom line?
It's been well-studied and proven that companies without consistent brand awareness efforts will see their lead generation efforts plateau and their acquisition costs grow substantially.
Part of the budget will have a direct impact on the P&L – events, paid advertisements, specific campaigns. Another part is spent on building awareness over the longer run.
At Pigment, we built an index that combined share of voice (coverage in the press), number of mentions from analysts, and increase in web traffic. You can aggregate a few KPIs to show the impact on awareness in the short term. Awareness efforts help pre-build and prepopulate the market. It will have an impact in the long term, but it requires a lot of education towards the board, especially as it involves significant investment that will likely pay back in a few years.
What I see is really two-thirds (of the marketing budget) on lead gen, one-third on awareness. Lead gen is how you're going to feed your pipeline for the next quarter. Awareness is how you're going to prep the market for the next year.
Third-party events are the ones you're going to buy from external suppliers, like Big Data London or Gartner events. Most of the time, they're unique, and when you get there, if you apply your normal ROI calculations, you're probably going to be disappointed. It’s better to view those events from the lens of brand awareness.
Then there are first-party events, like the events you can organise on your own that cost close to nothing and are often much more profitable. For physical events, I'd buy a few big third-party events where I know my ROI calculation is more brand awareness than leads (still necessary).
First-party events are much smaller, much quicker to organise, and there are many more of them, where you're going to have a real impact on pipeline and overall impact. This balance is probably not so well considered today by marketing leaders, but they should really give it some thought.
In marketing you need three things. If you want to run an F1 race, you're going to need to have an engine, a pilot, and fuel. To me, content is exactly like gasoline. You can have the best marketing organisation, the best marketing team players, but if you don't give them content, like a story, they're going to be unable to drive their car and to win any race, to be honest.
Sales
You should only hire your first salesperson when three things are true.One is you know your ICP, and you know it well.
The second is around the pipeline you have and your ability to generate it. You need to be capacity constrained in terms of your current ability to manage your pipeline and close deals.
The third thing is you need to know your sales process, at least at a high level. This means you need to have gone through a significant number of deals, end to end, as the founder, to understand and define the sales process.
There's two things I would think about in terms of identifying the right profile.
- One is what type of role you need. To identify this you need to look across your entire customer life cycle and sales pipeline and understand where the leverage is and where the bottlenecks in your process are.
- Once you have a clear idea of where there are bottlenecks and or upside from having more resource, then that is usually where you want to add the first resource. That means knowing what size of customer you're going to have them working with, and finding somebody with relevant experience with that size of customer, selling an analogous type of product as well as ideally dealing with the types of roles that your buyers are in, or as similar as possible.
The other general principle I have here is your first sales hire should have quite a broad skillset. Whilst you need a clear idea of who you are selling to and how you are selling to them, you will still be learning a lot and be building the plane as you fly it, so you need someone who can help with that.
For example, you might not have a sales deck or case studies. You want somebody who's able to work on fixing those things, building the process.
In your first sales hire you're looking to first understand how good a fit their background is versus your ICP.
For customer facing roles, I always like to do some kind of a written project. I think it's very difficult to test how structured somebody is in their thinking and communication without one. Most sales have quite a large element of emailing, so it’s going to be difficult for somebody to be really successful in a sales role if they can’t write and communicate properly.
Don't go too heavy on variable compensation or your first few hires. You’ll want them to have a fairly healthy equity package, and if they do a good job as the first salesperson, that equity will go up a lot in value as it is primarily driven by the revenue of the company, which is the sales person’s job to generate. The types of salespeople that want very high variable cash comp are usually not the right fit for what you need at this stage.
Jackie Karmel, Harvey and ex-Retool, Stripe
Ideally get into the habit of a weekly forecasting meeting where the sellers (or even just the founder) puts up the revenue number they’re committing to for the month and the key deals that’ll make up that number.Depending on your stage, forecasting a month out is helpful, e.g. commit for May is X and we’re going to deliver it with xyz opportunities. When you get a bit more confident in this approach and as the sales team scales, you can move to a quarterly forecasting motion, with regular check-ins weekly to ensure everyone is on track.
I’d expect 90% confidence levels for any deal you’re committing to deliver (sign) in a given month.
Ideally the pipeline review is the opportunity for the rep and the manager/founder to go deep on top deals in order to provide guidance and an extra layer of strategic thinking.
Customer Success can play a key role in forecasting since they are likely very in sync with how their customers buy, what the triggers are for expansion and any potential roadblocks to overcome in order to grow the account.
Lock-step partnership between Account Executives, Account Managers and Solution Engineers has never been more important to ensure a customer can grow in the timeframe you originally outlined when they first buy in to your product.
Dave Wyatt, ex Databricks, Mulesoft and Aiven
Then it was like an obvious lightning bolt that we need to figure out what the outcomes were of that business - which is solution selling on steroids, really.We thought about what the outcomes actually are. But we didn't just think about selling the outcome. We said, how am I actually going to deliver the outcome? So we created two things.
One was outcome based selling, the other piece was outcome based delivery. Then we build a conjoined plan with the customer of how they're going to get to the actual outcome.
You see most salespeople in particular who close plans, and then they don't care about what the customer is trying to achieve.
With outcome based selling, you had a mutual success plan which ended in the customer receiving their outcome and working backwards from that.
And outcome based selling was basically built around that framework. And the partnership with the customer was therefore much more strategic. The ASP went up by about 10x within months.
25 years ago, people had spent a year and a half trying to close a big deal. That was the reality. Maybe twelve months if they’re good. And if you were really lucky, six months.
So you'd spend twelve months working a deal as a salesperson. Now the reality is in a consumption world, you can get a customer using your technology really quickly. Now they might spend five grand a month, but that's absolutely fine because then the job of the salesperson now is to understand the projects that the customer is trying to deliver.
Now the salesperson is not interested in getting their deal, running away, and buying the Porsche 911. What they're actually interested in is this continued relationship that never ends.
The behavior is different now because they're interested in the outcome of the customer. Because they know if the customer is successful, they'll continue to do well. And if I'm the customer, I want to know - my salesperson wants to make me successful.
Community and PLG
Ben Lang, ex Head of Community at Notion
Our Ambassador program brought together our biggest advocates who would spread and teach Notion in incredible ways around the world. Some hosted gatherings, some wrote books about notion, some had youtube channels about notion, etc. ultimately they represented a subset of our most dedicated power users who had their own needs which at times would differ from our team customers.On the community team, we did end up building what we called our Champions program which brought together our biggest “internal” advocates which differed quite a bit from the external facing Ambassadors mentioned above. These internal advocates were the ones advocating for Notion on their teams. Depending on the company size, you might have one or a handful at a company. We wanted to make sure we could funnel in their feedback which oftentimes would include a lot of the feedback they were hearing internally from their teammates as the informal representatives of notion on their teams.
For starters, we had a lot of challenges with data given our decentralised approach with community building. Since all of the groups people created were community-led, we didn’t have the data access to connect to our own systems. We had to create our own custom tool for tracking the growth, engagement and impact of these groups, but there were still a lot of missing pieces.
When it came to influencer marketing, it was much easier to measure and track the impact on a regional level. In my article linked above about influencer marketing, I spoke about the flywheel between influencer marketing and participation in community programs. As we would go after certain markets, this flywheel would feed itself and have a visible impact. For example, in some countries we would kick off with a few influencer partnerships, we would see someone create a local Notion group and join our Ambassador program, more local users would join the group and participate in any local events, and more influencers would hear about Notion. This was incredible to see.
Notion's community is very vibrant. Our early focus on connecting with users and maintaining strong two-way communication has led to users building our product with us. We now have over a million community members and the largest subreddit.Our ambassador program has been instrumental in bridging the gap from our self-service business to our growing enterprise business. Community members often understand Notion deeply, figuring out functionalities we haven't even discovered. Many larger customers employ community members as consultants for onboarding and training, significantly reducing enterprise clients' ownership costs.
This organic process helps new users become proficient with Notion quickly, accelerating adoption and maximising value for organisations. CTOs and technology buyers want to minimise shelfware, and high adoption and utilisation are key. This program has been particularly effective in EMEA, where we've seen strong growth in our enterprise product and adoption.
Users take pride in generating templates for their work processes and love sharing them. For almost any task in Notion, there's likely a template available.
The community has been a tremendous asset in our upmarket move. The wealth of templates and use cases showcases Notion's versatility and potential to enterprise customers. In sales conversations, we often reference how other companies creatively use Notion, which resonates with potential enterprise customers. The community's enthusiasm serves as a powerful testimonial to Notion's value proposition. This synergy is very helpful for our sales team.
My advice to PLG founders would be to prepare for enterprise customers earlier in their journey. This includes product features and building necessary sales, support, and success teams. Crucially, maintain your product philosophy's core values that drove initial success. The key is evolving your offering without losing sight of what made your product special.
Solutions Engineering
Zaki Bajwa, Sprinklr and ex-Snyk, Stripe, ServiceNow
To use an american football analogy, most of sales happens in between the 20 yards, right? So first 20 yards is where the introduction happens, and the last 20 yards is where the procurement and the contract happens, but the main execution is in the middle. That's where the SE comes in, where they're building a tech champion.They're making sure there's vision alignment, they're making sure there's solution alignment. There's realisation of ‘how do I get this deployed, how do I get to value?’. SEs own the tech champion relationship which is critical for this middle phase of the sales cycle and, just as important, 90% of future customer references will be done by these tech champions.
The reason Fortune 2000 companies interact with SEs more is that they want SEs to really guide them, consult them, prescribe for them.
If you're launching a new product, the SE team has a nose to the ground and they can tell you whether product market fit is landing, if pricing is working.
I always tell SEs that if you're in the same meeting with your AE 80% of the time, then you're doing something wrong. You should be able to divide and conquer.
AEs take a client to a vision match in an early sales cycle with executives. The executives, a lot of times, are going to lean on technical champions or CIOs, as we were talking about earlier.
That's where the SE needs to get that mind share while the AE is getting more senior exec mind share, and then bring those together.
Partnerships
Stefan Ross, ex-Pigment and Celonis
My view is that partnerships is the umbrella term which encompasses cloud and marketplace partnerships, tech partnerships, and consulting partnerships.Alliances are more strategic.
It refers generally to large important individual partners, often referral/co-sell relationships, whereas partnerships is the umbrella term which can contain everything (types of partner and different GTM motions with them).
Consultants are invariably involved in software purchasing cycles, whether we want to engage or not. They are particularly prevalent within enterprise segments as tools are bought as part of a transformation story.
Upmarket, consultants will act as a trusted advisor to executives with a position to inform + educate which often translates into advisory work, change management and implementation. They understand intimately the fundamental problems of the business (e.g., CFO - profitability, working capital optimisation, cashflow preservation etc.) and can translate this into a tooling requirement on a multi-tech stack, think ERP, CRM, EPM etc. They often view individual software as a supporting component within their tool box.
Partners can help sell bigger (especially multi use-case), quicker, and with higher win rates as value can be more precisely communicated.
To be successful in partnering, the GTM organisation needs to be set up for this win-win. You can’t look to scale professional services whilst seeing partners as a vehicle to bring business and help. Incentives aren’t aligned…
Sometimes partnering with another vendor to offer a ‘complete solution’ with the help of a consultancy to articulate the ‘why’ can be lucrative, especially if playing against broad platform tools.
And I think what most organisations find is that they need to partner with those strategic consulting players.
Look at SAP, they transcend multiple tech stacks.
Look at the size of SAP practices at Deloitte, at KPMG, at Accenture. Huge.
If you have a great product and you're moving to becoming multiproduct, the premise is the exact same - you can have a slightly bigger piece of the transformation.
There are individual member firms which on a country level have a lot of autonomy. And in some, there will be independent entities. Then you have individuals who are striving to become a Partners in that organisation.
Their structural model is built in a way that they're always looking for the next best thing and they have to maintain their relevance for their customers.
Do they sit in risk advisory? Do they sit somewhere else? You're looking for those people that will be willing to take up a bet, if you like, on your tool, your technology.
Customer Success
So I actually have a really provocative, strong view that we're coming to the end of having a customer success department or a customer success function in organisations. To drive true net retention you need to be earlier in that customer lifecycle - it's not just a post-sales event.Everything you do needs to be focused on the customer's outcome. Designing the product, the roadmap, integrating AI into your solution, all of those things. Customer success, a skill set is still required.
Retaining customers and getting them to success with their outcomes is super important, but I think you'll find it will become much more customer journey focused. You’ll have the right person at the right time rather than a sort of generalist CSM role in the future.
We decided that having a CS function separate from our sales engineering function wasn't really working for our customers in a consumption world, because we don't really have pre and post-sales - in a consumption world, it is a continuum.
What we actually found is when we looked at the customer journey and where those tasks were required, we could focus individuals into those roles. They mapped quite well into other parts of organisation anyway, so we ended up splitting the CSM into three discrete roles.
We have a shared technical services team now that's very focused on onboarding customers. That's a point in time thing - just get them up and running, help them with the DevOps at the start.
We have a very big training team with a very strong curriculum on AI and Databricks. So we have a bunch of folks in there that help our customers build learning maps, integrate with their learning solutions, and help people build their careers with Databricks and get certified.
Then the third function was the Delivery Solution Architects that we that we designed to work with our customers once they decided to use Databricks. So from what we call a technical win through to production, and they work in that space.
The constant is our solution engineer, which we call a solution architect, and our account execs. We have a two in a box on every account, AE+SA. And then we have this specialist team that's available maybe for 30, 40, 50% of our customers. What we had to do was design the touch points of the customer journey and the tasks so that we became more of a team and we were able to pass the ball fluidly between the teams.
We've been on a journey this year. So our CSMs and CSEs historically were on a corporate bonus structure. We've seen in the shift to consumption that actually everyone is aligned to incremental consumption growth.
So net retention of consumption, gross retention of consumption are very important metrics for us. And we use net retention and gross retention across a number of leading indicator metrics that show us that the key metrics are users, learners, logins. If those change, then it has a downstream impact on consumption. But we've now aligned everyone on consumption.
Our product team actually ignore the field to speak to customers, which I think is a really healthy thing. So our PMs don't go through the account exec to speak to a customer. They just have a direct relationship.
I think that accelerates innovation and then we create new product for those customers and the product ships through the field to customers and then gets released. So there's a huge amount going on. I mean, at any stage, there are lots and lots of private previews in flight with customers.
BizOps
As companies grow, BizOps bridges the gap between organisational structure and business objectives – in other words, flexing into roles that aren’t yet proven out or hired for.My role for the first six months was to set up Salesforce, run quota models, prioritise accounts—basically, lay the groundwork for the sales process. I did this until we had about 30 sales reps and eventually hired a sales ops team.
Similarly with marketing, before we had a growth marketing function, I ran our first ads, set the budget, and tested platforms like Facebook, Instagram, Twitter, and LinkedIn. Once we saw the value, we hired a dedicated growth marketer.
Later, as we approached the pre-IPO stage, BizOps shifted toward long-term strategic planning. We started thinking about different sales motions, tapping into international markets, and evolving pricing frameworks as we became more of a multi-product platform.
The role requires a high comfort level with ambiguity. You need to be able to connect different parts of the business and navigate competing priorities. This is different from more specialized roles like sales ops or marketing ops, which are focused on specific functions.
As for timing, there should be some level of product-market fit first and I generally advise founders to hire for this role sooner rather than later. It’s easier for someone to scale with the company than to bring them in too late and have them play catch-up–-or worse, need to rip things out.
If it’s your first BizOps hire, I’d recommend bringing in someone with enough experience to provide strategic oversight but importantly still willing to get their hands dirty to execute themselves—really, someone who can grow alongside the company.
I like to think about how much leverage the team provides. Are they involved in high-level strategic decisions, or are they getting stuck in low-impact tasks? This is where I often see BizOps teams go wrong—when they grow too large and start working on low-priority tasks that don’t really move the needle.
So, the focus should be on how well their cross-functional partners are performing and how effectively the BizOps team is being leveraged across the organization.
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